Quaternary ammonium compounds

ABSTRACT

Drugs useful for the treatment and prevention of hyperlipidemia, moreover drugs useful for the treatment and prevention of cholestasis-caused hepatopathy, particularly primary biliary cirrhosis and primary sclerosing cholangitis, and drugs for the treatment and prevention of obesity, fatty liver and steatohepatitis, containing as active ingredients benzothiazepine compounds having a thioamide bond and a quaternary ammonium substituent, represented by formula (1) below are provided. 
                         
Also, drugs containing ileal bile acid transporter inhibiting compounds as active ingredients for the treatment and prevention of cholestasis-caused hepatopathy are provided.

DESCRIPTION OF RELATED APPLICATIONS

This application claims priority under 35 U.S.C. § 119 to Japanese Patent Application No. 2002-248586 filed on Aug. 28, 2002, Japanese Patent Application No. 2002-364725 filed on Dec. 17, 2002, U.S. Provisional Application Ser. No. 60/407291 filed Sep. 3, 2002, and U.S. Provisional Application Ser. No. 60/434416 filed Dec. 19, 2002. The contents of these applications are incorporated herein by reference.

BACKGROUND OF THE INVENTION

1) Field of the Invention

The present invention relates to novel benzothiazepine compounds having a thioamide bond and a quaternary ammonium substituent and to pharmaceutical compositions which contain them. Moreover, the present invention relates to pharmaceutical compositions for the treatment of cholestasis-caused hepatopathy and the like.

2) Description of the Related Art

Hyperlipidemia means a state where neutral fat, cholesterol and the like in blood are at higher levels than the normal levels and has been known to deserve a treatment since it is a main risk factor in ischemic diseases. Moreover, hyperlipidemia is also known to cause arteriosclerosis and in particular, to decrease blood cholesterol level is effective for the prevention and treatment of arteriosclerosis. Arteriosclerosis is also known as a cause of myocardial infarction cerebral thrombosis, peripheral arterial obstruction, and arteriosclerosis obliterans. Syndrome X was advocated by Reavens et al. (“Diabetes”, 37, 1595-1607, 1988) and means a multiple risk factor syndrome which develops arteriosclerosis by accumulation of risk factors such as hyperinsulinemia, hyperlipidemia, hypertension, and abnormality of glucose tolerance on an individual, although the factors are not so serious as to indicate the conditions of diseases when they exist independently of each other. A cholesterol-lowering agent is considered to be effective for the prevention or treatment of these diseases (Japan Clinical Hyperlipidemia - Volume 1 -ISSN0047-1 852).

At present, commercially available drugs for the treatment of hyperlipidemia include HMG-CoA reductase inhibitors, anion exchange resins and so forth. These drugs are used for the prevention and treatment of hyperlipidemia, in particular, hypercholesterolemia and arteriosclerosis. Furthermore, these drugs are also used in the prevention or treatment of myocardial infarction, cerebral thrombosis, peripheral arterial obstruction, and arteriosclerosis obliterans, which are diseases caused by hypercholesterolemia or arteriosclerosis.

SUMMARY OF THE INVENTION

It has heretofore been demanded to provide novel drugs useful as therapeutic and prophylactic agents for hyperlipidemia, and furthermore drugs which are also useful as therapeutic and prophylactic agents for cholestasis-caused hepatopathy, in particular primary biliary cirrhosis, and primary sclerosing cholangitis, as well as drugs which are useful as therapeutic and prophylactic agents for obesity, fatty liver, and steatohepatitis.

To solve the above-mentioned problem, the inventors of the present invention synthesized various compounds and studied their activity. As a result, they have verified that novel benzothiazepine compounds represented by formula (1) below having a thioamide bond and a quaternary ammonium substituent have high therapeutic and preventive effects for hyperlipidemia and moreover extremely potent ileal bile acid transporter inhibiting activity and blood cholesterol-lowering activity, so that they can be used as cholesterol-lowering agents, in particular as a therapeutic agent and preventive agent for hyperlipidemia, arteriosclerosis, syndrome X, etc. Furthermore, the inventors have verified that the novel benzothiazepine compounds have therapeutic and preventive effects for cholestasis-caused hepatopathy, so that the compounds can be used as therapeutic and preventive agents for cholestasis-caused hepatopathy, particularly for primary biliary cirrhosis and primary sclerosing cholangitis. Also, the inventors have verified that the compounds have a body weight reducing effect and a fatty liver improving effect, so that they can be used as therapeutic and preventive agents for obesity and fatty liver. Moreover, the inventors have verified that the compounds have a therapeutic effect and preventive effects for steatohepatitis, so that they can be used as therapeutic and preventive agents for steatohepatitis.

That is, the present invention provides a compound represented by formula (1) below.

[wherein R¹ and R², which may be mutually different, each represents an alkyl group having from 1 to 10 carbon atoms;

m represents an integer of 1 or 2, and R³ and R⁴, which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms;

Y represents any one of —NHCS—, —NHCSNH—, and —NHCSO— where the —NH in the —NHCS— represents a bond which links with an adjacent benzene ring and the CS— in the —NHCS— represents a bond which links with an adjacent Z, and the —NH in the —NHCSO— represents a bond which links with an adjacent benzene ring and the OSO— in the —NHCSO— represents a bond which links with an adjacent Z;

Z—(N⁺R⁵R⁶R⁷)_(n) represents an alkyl group having from 2 to 10 carbon atoms or an alkenyl group having from 2 to 10 carbon atoms which is substituted with n (—N⁺R⁵R⁶R⁷)s, where at least one of methylenes which constitute Z may be replaced by any one of a phenylene and an —O—;

n is an integer of 1 or 2; and

N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent:

I) R^(5,) R^(6,) and R⁷, which may be mutually different, each represents any one of an alkyl group having from 1 to 10 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, and an alkynyl group having from 2 to 10 carbon atoms, where the alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CON H₂ group, an —SO₃H group, and further, at least one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰— where R⁸ represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms and the alkyl group and alkenyl group represented by R⁸ may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group; R⁹ and R¹⁰ which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group; and W⁻represents a counter anion,

II) N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring which is formed by 4 to 9 carbon atoms in addition to an ammonium nitrogen atom, provided that the position of its bonding with Z is the ammonium nitrogen atom, where one of the carbon atoms which constitute the ring in the monocyclic ring and bicyclic ring may be replaced by any one atom of oxygen, nitrogen, and sulfur, and moreover, the monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a thioxo group, a cyano group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a carboxyl group, a —CON H₂ group, an —SO₃H group, and an —R¹¹group; R¹¹ represents an alkyl group having from 1 to 8 carbon atoms or an alkenyl group having from 2 to 8 carbon atoms, where the alkyl group and the alkenyl group represented by R¹¹ may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group; moreover, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N³⁰ W⁻R⁹R¹⁰—, where R⁸, R⁹ , R¹⁰, and W⁻are as described above; among R⁵, R⁶, and R⁷, those groups which are not involved in formation of the monocyclic ring and the bicyclic ring are the same as those in I) described above,

III) N⁺R⁵R⁶R⁷ represents a pyridinium ring, a quinolinium ring, or an isoquinolinium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the pyridinium ring, the quinolinium ring, and the isoquinolinium ring may be substituted with at least one of a cyano group, a nitro group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, an alkoxy group having from 1 to 5 carbon atoms, a carboxyl group, a —CONH₂ group, an —SO₃H group, and an —R¹² group; R¹² represents an alkyl group having from 1 to 9 carbon atoms or an alkenyl group having from 2 to 9 carbon atoms; and the alkyl group and the alkenyl group represented by R¹² may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group; and further, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—, where R⁸, R⁹, R¹⁰, and W⁻ are as described above, and X represents a counter anion].

Further, each of the substituents will be explained as follows.

R¹and R², which may be mutually different, each represents a straight chain or branched alkyl group having from 1 to 10 carbon atoms. Particularly, a straight chain alkyl group having from 1 to 10 carbon atoms is preferable and a straight chain alkyl group having from 2 to 6 carbon atoms is more preferable. Preferably R¹ and R² are mutually different and more preferably R¹and R² are the same alkyl groups. Specific preferable modes of R¹and R² include one in which both R¹and are an n— propyl group, an n— butyl group, an n— pentyl group, or an n— hexyl group, or one in which R¹ is an ethyl group and R²is an n— butyl group.

(NR³R⁴)_(m) means that any one of the 6-position to the 9-position is substituted with m (NR³R⁴)s. m is an integer of 1 or 2. Either 1 or 2 is preferable, with 1 being more preferable. Regarding the position of substitution, when m is 1, the 7-position or the 9-position is preferable, with the 7-position being more preferable; and when m is 2, it is preferable that the two positions consisting of the 7-position and the 9-position are substituted with the same NR³R⁴. R³ and R⁴, which may be mutually different, each represents a straight chain or branched alkyl group having from 1 to 5 carbon atoms. In particular, a straight chain alkyl group having from 1 to 3 carbon atoms is preferable, a methyl group or an ethyl group is more preferable, and a methyl group is most preferable. Specific preferable modes of (NR³R⁴)_(m) include a 7-dimethylamino group, a 7-diethylamino group, a 7-ethylmethylamino group, a 9-dimethylamino group, and a 7,9-bis (dimethylamino) group.

Y represents any one of an —NHCS—, an —NHCSNH—, and an —NHCSO—. Here, the —NH in the —NHCS— represents a bond which links with an adjacent benzene ring and the CS — represents a bond which links with an adjacent Z, and the —NH in —NHCSO— represents a bond which links with an adjacent benzene ring, and the OSO — represents a bond which links with an adjacent Z. Regarding Y, particularly preferable is —NHCS — or —NHCSNH—, with —NHCSNH — being particularly preferable; the position of its substitution on the benzene ring is any one of an ortho-position, a meta-position, and a para-position. A meta- or para-position is preferable, and a meta-position is most preferable.

Z-(N⁺R⁵R⁶R⁷)_(n) is an alkyl group having from 2 to 10 carbon atoms or an alkenyl group having from 2 to 10 carbon atoms which is substituted with n (-N⁺R⁵R⁶R⁷)s and at least one of methylenes which constitute Z may be replaced by any one of a phenylene and an —O—; n is an integer of 1 or 2, both 1 and 2 are preferable, and 1 is more preferable.

Among the alkyl groups having 2 to 10 carbon atoms and alkenyl groups having from 2 to 10 carbon atoms that are substituted with n (-N⁺R⁵R⁶R⁷)s, a straight chain or branched alkyl group having from 2 to 10 carbon atoms is preferable, and a straight chain alkyl group having from 2 to 10 carbon atoms or a branched alkyl group having from 3 to 7 carbon atoms is more preferable. When the alkyl group or the alkenyl group is substituted with one -N⁺R⁵R⁶R⁷, both the straight chain alkyl group having from 2 to 10 carbon atoms and the branched alkyl group having from 3 to 7 carbon atoms are preferable and the straight chain alkyl group having from 2 to 10 carbon atoms is more preferable. When the alkyl group or the alkenyl group is substituted with two (-N⁺R⁵R⁶R⁷)s, a branched chain alkyl group having from 3 to 6 carbon atoms is preferable. In the case of the straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one -N⁺R⁵R⁶R⁷, it is particularly preferable that Z represents a straight chain methylene group having from 2 to 10 carbon atoms.

It is preferable that the at least one of methylenes which constitute Z is replaced by any one of a phenylene and an —O—; however, more preferably the at least one of methylenes is not at all replaced when Y represents —NHCS—. When Y represents —NHCSNH—, more preferably the at least one of methylenes is replaced by a phenylene and a preferable mode of Z in this case is as mentioned earlier. Even when the at least one of methylenes which constitute Z is replaced by any one of a phenylene and an —O—, a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one -N⁺R⁵R⁶R⁷, is preferable, and it is particularly preferable that Z represents a straight chain methylene group having from 2 to 10 carbon atoms. A preferable mode of replacement is any one of replacement of one methylene by a phenylene, replacement of one methylene by an —O—, and replacement of one methylene by a phenylene and another methylene by an —O—. A more preferable mode of replacement is replacement of one methylene by a phenylene. However, the —O— by which one methylene is replaced referred to herein is different from the oxygen atom in the —NHCSO — represented by Y. The phenylene is any one of those represented by the following formulae (phe-1), (phe-2), and (phe-3), among which the formulae (phe-1) or (phe-2) is preferable, and the formula (phe-1) is more preferable.

Replacement of at least one of methylenes by a phenylene or an —O— is, for example, as illustrated in a figure below.

Specific preferable modes of Z include formulae from (sp-1) to (sp-22) and further formulae from (sp-23) to (sp-25) below. In the formulae, *a is bonded to Y in the formula (1) and *b is bonded to N⁺R⁵R⁶R⁷. The formulae (sp-19) and (sp-20) are specific examples when n is 2 and the remaining formulae are specific examples when n is 1.

When Y represents —NHCS—, it is particularly preferable that Z is represented by any one of formulae from (sp-1) to (sp-10), from (sp-14) to (sp-16), (sp-18), (sp-19), (sp-21), and (sp-22); among these, the formulae from (sp-1) to (sp-9) are more preferable and (sp-4) is most preferable. When Y represents —NHCSNH—, it is particularly preferable that Z is represented by any one of the formulae from (sp-1) to (sp-9), from (sp-12) to (sp-14), (sp-17), and (sp-20) and the formulae from (sp-23) to (sp-25) are also particularly preferable. Among them, the formulae (sp-1) to (sp-9), and further (sp-14), or (sp-23), and (sp-24), are more preferable, with (sp-14) being most preferable. When Y represents —NHCSO—, it is particularly preferable that Z is any one of the formulae from (sp-1) to (sp-9) and (sp-11); among these, the formulae from (sp-1) to (sp-9) are more preferable.

N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent.

I) R⁵, R⁶, and R⁷, which may be mutually different, each represents an alkyl group having from 1 to 10 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, or an alkynyl group having from 2 to 10 carbon atoms. The alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CON H₂ group, and an —SO₃H group, and further, at least one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—. R⁸ represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. R⁹ and R¹⁰, which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. W⁻ represents a counter anion.

When R⁵, R⁶, and R⁷ each represents an alkyl group, the alkyl group has preferably from 1 to 10 carbon atoms, any one of 1 to 10 is preferable as the number of carbon atom(s), and more preferably the alkyl group is a straight chain alkyl group having from 1 to 10 carbon atoms. Specific preferable examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an i—butyl group, an n-pentyl group, an —pentyl group, an n-hexyl group, a 3,3-dimethylbutyl group, an n-heptyl group, a 2,2-dimethylpentyl group, an n-octyl group, an n-nonyl group, an n-decanyl group, and a 2,3-diethylhexyl group. When R⁵, R⁶, and R⁷ each represents an alkenyl group, the alkenyl group has preferably from 3 to 8 carbon atoms, and more preferably the alkenyl group is a straight chain alkenyl group having 3, 4, 5, 6, or 8 carbon atoms or a branched alkenyl group having 4, 6, or 7 carbon atoms. Specific preferable examples of the alkenyl group include a 2-propenyl group, a 2-methyl-2-propenyl group, a 3-butenyl group, a 4-pentenyl group, a 4-methyl-4-pentenyl group, a 5-hexenyl group, a 2-hexenyl group, a 5-methyl-5-hexenyl group, and a 2,7-octadienyl group. When R5, R6, and R7 each represents an alkynyl group, the alkynyl group has preferably from 3 to 9 carbon atoms, and more preferably the alkynyl group is a straight chain alkynyl group having 3, 5, 6, 7, or 9 carbon atoms or a branched alkynyl group having 6 carbon atoms. Specific preferable examples of the alkynyl group include a 2-propynyl group, a 2-pentynyl group, a 4-methyl-2-pentynyl group, a 2-hexynyl group, a 2-heptynyl group, and a 2-nonynyl group.

These preferable alkyl groups, alkenyl groups, and alkynyl groups, particularly alkyl groups, may be substituted with at least one of a phenyl group, a thienyl group, a cyclohexyl group, a cyano group, a hydroxyl group, an oxo group, a carboxyl group, a —CON H₂ group, and a —SO₃H group. Moreover, at least one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly at least one of methylenes which constitute the alkyl group, may be replaced by any one of a phenylene, a thienylene, a furylene, an —O—, a —CO₂—, an —NHCO—, an —NR⁸— (where R⁸ represents an alkyl group having from 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms, preferably a straight chain alkyl group having from 1 to 3 carbon atoms or a straight chain alkenyl group having 3 carbon atoms, and the alkyl group may be substituted with at least one of a phenyl group and a hydroxyl group), and an —N⁺W⁻R⁹R¹⁰— (where R⁹ and R^(10,) which may be mutually different, each represents an alkyl group having from 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms, preferably a straight chain alkyl group having from 1 to 3 carbon atoms or a straight chain alkenyl group having 3 carbon atoms, and the alkyl group may be substituted with at least one of a phenyl group and a hydroxyl group). It is more preferable that the alkenyl group and the alkynyl group are neither substituted nor replaced.

More preferable modes include any one of 1) a mode in which the preferable alkyl group, alkenyl group, and alkynyl group, in particular the alkyl group, represented by R⁵, R⁶, and R⁷ is substituted with any one of a phenyl group, a thienyl group, a cyclohexyl group, a cyano group, a hydroxyl group, an oxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group, 2) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with two hydroxyl groups, 3) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group and one —SO₃H group, 4) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one oxo group and one phenyl group, 5) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group and two phenyl groups, 6) a mode in which one methylene which constitutes the alkyl group, the alkenyl group, and the alkynyl group, particularly at least one of methylenes which constitute the alkyl group is replaced by any one of a phenylene, a furylene, a —CO₂—, an —NHCO—, an —NR⁸— (where R⁸ represents any one of a straight chain alkyl group having from 1 to 3 carbon atoms, a straight chain alkenyl group having 3 carbon atoms, a straight chain alkyl group having from 1 to 3 carbon atoms which is substituted with one hydroxyl group, and a straight chain alkyl group having from 1 to 3 carbon atoms which is substituted with one phenyl group, with specific examples thereof including a methyl group, an ethyl group, an n-propyl group, a 2-propenyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, and a benzyl group), and an —N⁺W⁻R⁹R¹⁰— (where R⁹ and R¹⁰, which may be mutually different, each represents a straight chain alkyl group having from 1 to 3 carbon atoms, a straight chain alkenyl group having 3 carbon atoms, a straight chain alkyl group having from 1 to 3 carbon atoms which is substituted with one hydroxyl group, and a straight chain alkyl group having from 1 to 3 carbon atoms which is substituted with one phenyl group, with specific examples thereof including a methyl group, an ethyl group, an n-propyl group, a 2-propenyl group, a 2-hydroxyethyl group, and a benzyl group), 7) a mode in which two methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly two methylenes which constitute the alkyl group are replaced by any one selected from two (—O—)s, one phenylene and one —O—, one —O— and one —NR⁸—, and one —NHCO — and one —O—, 8) a mode in which three methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly three methylenes which constitute the alkyl group are replaced by two (—O—)s and one —NR⁸, or one phenylene and two (—NHCO—)s, 9) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes which constitute the alkyl group is replaced by an —O—, 10) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes which constitute the alkyl group is replaced by an —NR⁸—, 11) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group, and moreover one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes which constitute the alkyl group is replaced by a furylene, 12) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one oxo group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes which constitute the alkyl group is replaced by a thienylene, 13) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one oxo group, and moreover, two of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly two of methylenes which constitute the alkyl group are replaced by one —O— and one phenylene, or the preferable alkyl group, alkenyl group, and alkynyl group represented by R⁵, R⁶, and R⁷ are neither substituted nor replaced.

In the most preferable mode, R⁵, R⁶, and R⁷ each represents any one of a straight chain alkyl group having from 1 to 10 carbon atoms, a straight chain alkyl group having from 1 to 10 carbon atoms which is substituted with one phenyl group, a straight chain alkyl group having from 1 to 10 carbon atoms which is substituted with one hydroxyl group, a straight chain alkenyl group having from 3 to 6 or 8 carbon atoms, a branched alkenyl group having 4, 6, or 7 carbon atoms, a straight chain alkynyl group having 3, 5, 6, 7, or 9 carbon atoms, and a branched alkynyl group having 6 carbon atoms.

Specifically, N,N-dimethyl-N-(n-hexyl)ammonium, N-benzyl- N,N-dimethylammonium, N-benzyl-N-methyl -N-(propargyl)ammonium, or N,N-dimethyl-N-(n-butyl)ammonium is preferable, and N-benzyl- N,N-dimethylammonium or N-benzyl -N-methyl-N-propargylammonium is particularly preferable.

II) —N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring which is formed by 4 to 9 carbon atoms in addition to an ammonium nitrogen atom, provided that the position of its bonding with Z is the ammonium nitrogen atom. In the monocyclic ring and the bicyclic ring, one of the carbon atoms which constitute the ring may be replaced by any one atom of oxygen, nitrogen, and sulfur, and moreover, the monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a thioxo group, a cyano group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a carboxyl group, a —CONH₂ group, an —SO₃H group, and an —R¹¹. R¹¹ represents an alkyl group having from 1 to 8 carbon atoms or an alkenyl group having from 2 to 8 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group. Moreover, at least one of methylenes which constitute the alkyl and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—. R⁸ represents an alkyl group or alkenyl group having from 1 to 5 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. R⁹ and R¹⁰, which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms, and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. W represents a counter anion. Among R⁵, R⁶, and R⁷, a group which is not involved in the formation of the monocyclic and the bicyclic ring represents an alkyl group having from 1 to 10 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, or an alkynyl group having from 2 to 10 carbon atoms. The alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group. Moreover, at least one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a naphthylene, a thienylene, a furylene, a pyridylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—. R⁸ represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. R9 and R10, which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms, and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. W represents a counter anion.

The monocyclic ring or bicyclic ring represented by the N⁺R⁵R⁶R⁷ is preferably any one of a pyrrolidinium ring, a piperidinium ring, a morpholinium ring, a thiomorpholinium ring, a piperazinium ring, an azepanium ring, a quinuclidinium ring, and a 1,4-diazabicyclo[2.2.2] octanium ring. The monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a cyano group, a phenyl group, a —CONH₂— group, and an —R¹¹. Here, R¹¹ is preferably an alkyl group having from 1 to 6 carbon atoms or an alkenyl group having 3 carbon atoms and more preferably a straight chain alkyl group having from 1 to 5 carbon atoms (for example, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, or an n-pentyl group), a branched alkyl group having 6 carbon atoms (for example, a 3,3-dimethylbutyl group), a straight chain alkenyl group having 3 carbon atoms (for example, a 2-propenyl group). The alkyl group may be substituted with at least one of a hydroxyl group, a cyano group, a phenyl group, and a —CONH₂ group. Moreover, at least one of methylenes which constitute the alkyl group may be replaced by any one of an —O—, a —CO₂—, and an —NHCO—. Among R⁵, R⁶, and R⁷, a group which is not involved in the formation of the ring represents an alkyl group having from 1 to 6 carbon atoms (preferably a straight chain alkyl group having from 1 to 6 carbon atoms), an alkenyl group having from 3 to 4 carbon atoms (preferably a straight chain alkenyl group having from 3 to 4 carbon atoms), or an alkynyl group having from 3 to 6 carbon atoms (preferably a straight chain alkynyl group having 3, 4, or 6 carbon atoms). The alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group may be substituted with at least one of a phenyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cyclopropyl group, a cyclopentyl group, a cyano group, a hydroxyl group, an oxo group, a nitro group, a carboxyl group, and an —SO₃H group. Moreover, at least one of methylenes which constitute the alkyl group may be replaced by any one of a phenylene, an —O—, and a —CO₂—. It is more preferable that the alkenyl group and the alkynyl group are neither substituted nor replaced.

In a more preferable mode, the pyrrolidinium ring, the piperidinium ring, the morpholinium ring, the thiomorpholinium ring, the piperazinium ring, the azepanium ring, the quinuclidinium ring, and the 1,4-diazabicyclo[2.2.2]octanium ring are 1) substituted with any one of a hydroxyl group, an oxo group, a cyano group, a phenyl group, a —CONH₂ group, and an —R¹¹ group, 2) substituted with one cyano group and one hydroxyl group, 3) substituted with one hydroxyl group and one —R¹¹, 4) substituted with one oxo group and one —R¹¹, 5) substituted with two oxo groups, or 6) substituted with two (—R¹¹)s. Alternatively, the pyrrolidinium ring, the piperidinium ring, the morpholinium ring, the thiomorpholinium ring, the piperazinium ring, the azepanium ring, the quinuclidinium ring, and the 1,4-diazabicyclo[2.2.2]octanium ring are unsubstituted. Here, R¹¹ represents a straight chain alkyl group having from 1 to 5 carbon atoms (for example, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, or an n-pentyl group), a branched alkyl group having 6 carbon atoms (for example, a 3,3-dimethylbutyl group), or a straight chain alkenyl group having 3 carbon atoms (for example, a 2-propenyl group), in which 1) the alkyl group is substituted with one hydroxyl group or one phenyl group, 2) one of methylenes which constitute the alkyl group is replaced by either a —CO₂— or an —NHCO—, 3) two methylenes which constitute the alkyl group are replaced by one —O— and one —NHCO—, 4) the alkyl group is substituted with one cyano group and moreover, one of methylenes which constitute the alkyl group is replaced by an —O—, 5) the alkyl group is substituted with one —CONH₂ and moreover, one of methylenes which constitute the alkyl group is replaced by an —O—, 6) the alkyl group is substituted with one phenyl group and moreover, one of methylenes which constitute the alkyl group is replaced by a —CO₂—, 7) the alkyl group is substituted with one phenyl group and moreover, one of methylenes which constitute the alkyl group is replaced by an —NHCO—, or 8) the alkyl group is neither substituted nor replaced. Specific examples of R¹¹ include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-propenyl group, a benzyl group, an acetylamino group, a t-butoxycarbonylamino group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-cyanoethoxy group, a (2-cyanoethoxy)methyl group, a 2-carbamoylethoxy group, an ethoxycarbonyl group, a t-butoxycarbonyl group, a benzoyloxy group, a phenylacetylamino group, a butanoylamino group, and a pentanoylamino group. Among R⁵, R⁶, and R⁷, a group which is not involved in the formation of the ring represents a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkenyl group having from 3 to 4 carbon atoms, or a straight chain alkynyl group having 3, 4, or 6 carbon atoms, in which 1) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with any one of a phenyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cyclopropyl group, a cyclopentyl group, a cyano group, a hydroxyl group, a carboxyl group, and an —SO₃H group, 2) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with two hydroxyl groups, 3) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group and one —SO₃H, 4) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with four hydroxyl groups and one oxo group, 5) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one nitro group and one morpholyl group, 6) one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes which constitute the alkyl group is replaced by a —CO₂—, or 7) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one morpholyl group and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes which constitute the alkyl group is replaced by an —O—, or the alkyl group, the alkenyl group, and the alkynyl group are neither substituted nor replaced.

A particularly preferable mode is one in which the ring is a pyrrolidinium ring, a piperidinium ring, an azepanium ring, a quinuclidinium ring, or a 1,4-diazabicyclo[2.2.2]octanium ring which is substituted with any one of a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-propenyl group, a phenyl group, a benzyl group, a hydroxyl group, a hydroxymethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group; or unsubstituted. Among R⁵, R⁶, and R⁷, a group which is not involved in the formation of the ring represents any one of a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkyl group having from 1 to 6 carbon atoms which is substituted with one phenyl group, a straight chain alkyl group which is substituted with one hydroxyl group, a straight chain alkenyl group having from 3 to 4 carbon atoms, and a straight chain alkynyl group having 3, 4, or 6 carbon atoms.

Regarding the group which is not involved in the formation of the ring, specific preferable examples of the straight chain alkyl group having from 1 to 6 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group; specific preferable examples of the straight chain alkenyl group having from 3 to 4 carbon atoms include a 2-propenyl group, a 3-butenyl group, and a 2,7-octadienyl group; and specific preferable examples of the straight chain alkynyl group having 3, 4, or 6 carbon atoms include a 2-propynyl group, a 2-butynyl group, and a 2,4-hexadiynyl group.

In the most preferable mode, the ring is a quinuclidinium ring or a 1,4-diazabicyclo[2.2.2]octanium ring which is either substituted with any one of an n-butyl group, a phenyl group, a benzyl group and a hydroxyl group, or unsubstituted.

Specifically, quinuclidinium-1 -yl, 4-phenylquinuclidinium-1 -yl, 3-hydroxyquinuclidinium-1-yl, 1 ,4-diazabicyclo[2.2.2]octanium-1 -yl, 4-n-butyl.-1 ,4-diazabicyclo[2.2.2]octanium-1 -yl, and 4-benzyl-1 ,4-diazabicyclo[2.2.2]octanium-1-yl are preferable, and particularly preferable examples include quinuclidinium-1 -yl, 4-phenylquinuclidinium-1-yl, and 1 ,4-diazabicyclo[2.2.2]octanium-1 -yl. Among these, 4-phenylquinuclidinium-1-yl is most preferable. Also, in some cases, 1,4-diazabicyclo[2.2.2]octanium-1-yl is most preferable. Furthermore, in some other cases, quinuclidinium-1-yl is most preferable.

In another most preferable mode, the ring is a pyrrolidinium ring, a piperidinium ring, or an azepanium ring which is either substituted with any one of a methyl group, a phenyl group, a benzyl group, a hydroxyl group, a hydroxymethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group, or unsubstituted. Among R⁵, R⁶, and R⁷, a group which is not involved in the formation of the ring represents any one of a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkyl group having from 1 to 6 carbon atoms which is substituted with one phenyl group, a straight chain alkyl group which is substituted with one hydroxyl group, a straight chain alkenyl group having from 3 to 4 carbon atoms, and a straight chain alkynyl group having 3, 4, or 6 carbon atoms. Specifically, 1 -methyl-pyrrolidinium-1 -yl, 1 -ethyl-pyrrolidinium-1-yl, 1 -n-butyl-pyrrolidinium-1-yl, 1-n-pentyl-pyrrolidinium-1 -yl, 3-hydroxy-1 -methyl-pyrrolidinium-1 -yl, 1-ethyl-3-hydroxy-pyrrolidinium-1-yl, 1-benzyl-3-hydroxy-pyrrolidinium-1-yl, 1-methyl-piperidinium-1-yl, 1-ethyl-piperidinium-1-yl, 1-n-butyl-piperidinium-1-yl, 1-n-pentyl-piperidinium-1-yl, 4-benzyl-1-n-butyl-piperidinium-1-yl, 4-benzyl-1-n-pentyl-piperidinium-1-yl, 3-hydroxy-1-methyl-piperidinium-1-yl, 4-hydroxy-1-methyl-piperidinium-1-yl, 3-hydroxymethyl-1-methyl-piperidinium-1-yl, 1-benzyl-4-hydroxymethyl-piperidinium-1-yl, 1-benzyl-4-hydoxyethyl-piperidinium-1-yl, 1-benzyl-4-hydroxy-piperidinium-1-yl, 1-ethyl-azepanium-1 -yl, 1-n-butyl-azepanium-1-yl, 1-n-pentyl-azepanium-1-yl, 1-benzyl-azepanium-1-yl, and 1-hydroxyethyl-azepanium-1-yl are preferable; 1-n-butyl-pyrrolidinium-1-yl, 1-ethyl-piperidinium-1-yl, 4-benzyl-1-n-butyl-piperidinium-1-yl, 4-benzyl-1-n-pentyl-piperidinium-1-yl, and 1-benzyl-4-hydroxy-piperidinium-1-yl are more preferable, with 1-benzyl-4-hydroxy-piperidinium-1-yl being most preferable.

III) N⁺R⁵R⁶R⁷ represents a pyridinium ring, a quinolinium ring, or an isoquinolinium ring, provided which the position of its bonding with Z is the ammonium nitrogen atom. The pyridinium ring, the quinolinium ring, and the isoquinolinium ring may be substituted with at least one of a cyano group, a nitro group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, an alkoxy group having from 1 to 5 carbon atoms, a carboxyl group, a —CONH₂ group, an —SO₃H group, and an group. R12 represents an alkyl group having from 1 to 9 carbon atoms or an alkenyl group having from 2 to 9 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, thioxo group, a carboxyl group, a —CON H2 group, and an —SO₃H group. Further, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —S — , a —CO₂—, an —NHCO— , an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—. R⁸ represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. R⁹ and R¹⁰, which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms, and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group W⁻ represents a counter anion.

It is preferable that among the pyridinium ring, the quinolinium ring, and the isoquinolinium ring, the pyridinium ring and the quinolinium ring, particularly the pyridinium ring, is substituted with at least one of a cyano group, a nitro group, a phenyl group, a thienyl group, a pyridyl group, an alkoxy group having from 1 to 3 carbon atoms, a carboxyl group, a —CONH2— group, and an —R¹² group. Here, R¹² represents an alkyl group having from 1 to 9 carbon atoms (preferably a straight chain alkyl group having from 1 to 7 carbon atoms, or a branched alkyl group having from 3 to 5 or 9 carbon atoms) or an alkenyl group having from 2 to 4 carbon atoms (preferably a straight chain alkenyl group having from 2 to 4 carbon atoms). The alkyl group and the alkenyl group, particularly the alkyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a cyano group, a nitro group, a hydroxyl group, an oxo group, a carboxyl group, and an —SO₃H group, and moreover, at least one of methylenes which constitute the alkyl group and the alkenyl group, particularly one of methylenes which constitute the alkyl group may be replaced by any one of an —S—, a —CO₂—, an —NHCO—, and an —NR⁸—, where R⁸ represents an alkyl group having from 1 to 3 carbon atoms (preferably a straight chain alkyl group having from 1 to 3 carbon atoms) and the alkyl group may be substituted with at least one (preferably one) hydroxyl group.

In a more preferable mode, the ring is any one of 1) a pyridinium ring substituted with any one of a cyano group, a phenyl group, a thienyl group, a pyridyl group, a methoxy group, an ethoxy group, a propoxy group, a carboxyl group, a —CONH²— group, and an —R¹² group, 2) a pyridinium ring substituted with two cyano groups, 3) a pyridinium ring substituted with two (—R¹²)s, 4) a pyridinium ring substituted with one cyano group and one —R¹², 5) a pyridinium ring substituted with one phenyl group and one —R¹², 6) a quinolinium ring substituted with any one of a cyano group, a nitro group, a carboxyl group, a methoxy group, an ethoxy group, a propoxy group, and an —R¹² group, 7) a quinolinium ring substituted with one methoxy group and one —R¹², 8) a quinolinium ring substituted with one nitro group and one —R¹², 9) an unsubstituted pyridinium ring, 10) an unsubstituted quinolinium ring, and 11) an unsubstituted isoquinolinium ring. Here, R¹² represents a straight chain alkyl group having from 1 to 7 carbon atoms (for example, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, or an n-heptyl group), a branched alkyl group having from 3 to 5 or 9 carbon atoms (for example, an i-propyl group, a t-butyl group, a 3-pentyl group, or a 5-nonyl group), , or a straight chain alkenyl group having 2 to 4 carbon atoms (for example, a vinyl group or a 3-butenyl group), and 1) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with any one of a phenyl group, a naphthyl group, a pyridyl group, a cyano group, a nitro group, a hydroxyl group, an oxo group, a carboxyl group, and an —SO₃H group, 2) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one oxo group and one phenyl group, 3) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with two hydroxyl groups and one one pyridyl group, 4) one of methylenes which constitute the alkyl group and the alkenyl group, particularly one of methylenes which constitute the alkyl group is replaced by a —CO₂—, 5) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one hydroxyl group and moreover, one of methylenes which constitute the alkyl group and the alkenyl group, particularly one of methylenes which constitute the alkyl group is replaced by an —NHCO—, 6) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one oxo group, and moreover, one of methylenes which constitute the alkyl group and the alkenyl group, particularly one of methylenes which constitute the alkyl group is replaced by a —CO₂—, 7) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one phenyl group, and moreover, one of methylenes which constitute the alkyl group and the alkenyl group, particularly one of methylenes which constitute the alkyl group is replaced by a —CO₂—, 8) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one carboxyl group, and moreover, one of methylenes which constitute the alkyl group and the alkenyl group, particularly one of methylenes which constitute the alkyl group is replaced by an —S—, 9) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one hydroxyl group and one oxo group, and moreover, one of methylenes which constitute the alkyl group and the alkenyl group, particularly one of methylenes which constitute the alkyl group is replaced by an —NR⁸— (where R⁸ represents a methyl group, an ethyl group, an n-propyl group, a 2-hydroxyethyl group, or a 3-hydroxypropyl group), or 10) the alkyl group and the alkenyl group are neither substituted nor replaced. Specific examples of R12 include a methyl group, an ethyl group, an n-propyl group, an -propyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a 3-pentyl group, a 5-nonyl group, a vinyl group, a benzyl group, a 3-phenylpropyl group, a 2-(1-naphthyl)vinyl group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a formyl group, an acetyl group, a propionyl group, a benzoyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, a hexoxycarbonyl group, a benzyloxycarbonyl group, a 2-propenyloxycarbonyl group, an ethoxycarbonylmethyl group, a 2-(methoxycarbonyl)ethyl group, an ethoxycarbonylmethylcarbonyl group, a 2-hydroxyethylaminocarbonyl group, a bis(2-hydroxyethyl)aminocarbonyl group, a 2-carboxyvinyl group, a carboxymethylthio group, a cyanomethyl group, a 2-nitrovinyl group, a 2-(4-pyridyl)ethyl group, a 2-(4-pyridyl)vinyl group, a 3-(4-pyridyl)propyl group, a 2-(4-pyridyl)-1,2-dihydroxyethyl group, and a 2-sulfoethyl group.

In a particularly preferable mode, the ring is any one of an unsubstituted pyridinium ring, an unsubstituted quinolinium ring, an unsubstituted isoquinolinium ring, a pyridinium ring substituted with any one of a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a vinyl group, a phenyl group, a benzyl group, a 3-phenylpropyl group, a hydroxymethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group, a pyridinium ring substituted with either two methyl groups or two ethyl groups, a pyridinium ring substituted with one phenyl group and one methyl group, and a quinolinium ring substituted with either one methyl group or one i-propyl group. In the most preferable mode, the ring is a pyridinium ring which is either substituted with any one of a t-butyl group, an n-butyl group, an n-propyl group, an ethyl group, a methyl group, a hydroxypropyl group, and a methoxycarbonylethyl group, or unsubstituted.

Specifically, isoquinolinium-1-yl, 4-methylpyridinium-1-yl, 3-(n-butyl)pyridinium-1-yl, 4-ethyl-pyridinium-1-yl, 4-(t-butyl)pyridinium-1-yl, 3-(3-hydroxypropyl)-pyridinium-1-yl, 3-(3-hydroxypropyl)-pyridinium-1-yl, 3-[2-(methoxycarbonyl)ethyl]- pyridinium-1-yl, and 2-(n-propyl)-pyridinium-1-yl are preferable, and 4-(t-butyl)pyridinium-1-yl, 3-(3-hydroxypropyl)-pyridinium-1-yl, 3-[2-(methoxycarbonyl)ethyl]-pyridinium-1-yl, and 2-(n-propyl)- pyridinium-1-yl are particularly preferable.

After all, the N⁺R⁵R⁶R⁷ is preferably one group selected from the group consisting of N-benzyl-N,N-dimethylammonium, N-benzyl-N-methyl-N-propargylammonium, 4-phenylquinuclidinium-1-yl, 1 ,4-diazabicyclo[2. 2.2]octanium-1-yl, 1-benzyl-4-hydroxy-piperidinium-1-yl, 4-(t-butyl)pyridinium-1-yl, 3-(3-hydroxypropyl)-pyridinium-1-yl, 3-[2-(methoxycarbonyl)ethyl]- pyridinium-1-yl, and 2-(n-propyl)-pyridinium-1-yl.

Examples of the naphthyl group used in the explanation from I) to Ill) above include a 1-naphthyl group and a 2-naphthyl group, with a 1-naphthyl group being preferable. Examples of the pyridyl group include a 1-pyridyl group, a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group, preferably a 1-pyridyl group and a 4-pyridyl group, and more preferably a 4-pyridyl group. Examples of the quinolyl group include a 1-quinolyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group, and a 8-quinolyl group, preferably a 1-quinolyl group and a 4-quinolyl group. Examples of the thienyl group include a 2-thienyl group and a 3-thienyl group, preferably a 2-thienyl group. Examples of the furyl group include a 2-furyl group, and a 3-furyl group, preferably a 2-furyl group. Examples of the piperidyl group include a 1-piperidyl group, a 2-piperidyl group, a 3-piperidyl group, and a 4-piperidyl group, preferably a 1-piperidyl group and a 4-piperidyl group, and more preferably a 1-piperidyl group. Examples of the pyrrolidyl group include a 1-pyrrolidyl group, a 2-pyrrolidyl group, and a 3-pyrrolidyl group, preferably a 1-pyrrolidyl group. Examples of the morpholyl group include a 2-morpholyl group, a 3-morpholyl group, and a 4-morpholyl group, particularly preferably a 4-morpholyl group. Preferable examples of the cycloalkyl group having from 3 to 7 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The phenylene group is represented by any one of the formulae (phe-1) to (phe-3) mentioned earlier and preferably the formula (phe-1) or (phe-2), and more preferably the formula (phe-1). The thienylene group is represented by any one of the formulae (thi-1) to (thi-4) given below, with the formula (thi-1) being particularly preferable.

The furylene group is represented by any one of the formulae (fur-i) to (fur-4) given below, with formula (fur-i) being particularly preferable.

The cyclohexylene group is represented by any one of the formulae (hex-1) to (hex-3) given below, preferably the formula (hex-1) or the formula (hex-2), and more preferably the formula (hex-1). The cyclopentylene group is represented by any one of the formulae (pen-1) and (pen-2) given below, preferably the formula (pen-1).

Specific examples of the —N⁺R⁵R⁶R⁷ which correspond to I) include the formulae (an-1) to (an-158) and further (an-380) and (an-381) given below.

Specific examples of the —N⁺R⁵R⁶R⁷ which correspond to II) include the formulae (an-159) to (an-299) and further (an-382) given below.

Specific examples of the —N⁺R⁵R⁶R⁷ which correspond to Ill) include formulae from (an-300) to (an-377), further (an-378), (an-379), and moreover (an-394) to (an-402) given below.

Specific examples of the —N⁺R⁵R⁶R⁷ other than those which correspond to I) to III) above include the formulae (an-383) to (an-393) and further (an-403) to (an-407) given below.

W⁻ and X⁻ each represents a counter anion which may be negatively charged ions regardless of their valence and can electrically neutralize a positively charged ammonium ion in the compound of the present invention, and it is preferable that they are pharmaceutically acceptable anions. Examples of preferable anion include F⁻, Cl⁻, Br⁻, I⁻, OH⁻, CH₃SO₃ ⁻, CF₃SO₃ ⁻, HCO₂ ⁻, CH₃CO₂ ⁻, CF₃CO₂ ⁻, ClO₄ ⁻, IO₄ ⁻, HCO₃ ⁻, CO₃ ²⁻, NO₃ ⁻, HSO₄ ⁻, SO₄ ²⁻, H₂PO₄ ²⁻, HPO₄ ²⁻, PO₄ ³⁻, among which Cl⁻and Br⁻ are particularly preferable. W⁻ and X⁻ may be mutually different but more preferably they are the same.

Combinations of the substituents are not particularly limited; examples of particularly preferable compounds include

(1) compounds in which Z-(N⁺R⁵R⁶R⁷)_(n) represents an alkyl group having 2 to 10 carbon atoms which is substituted with n (—N⁺R⁵R⁶R⁷)s and at least one of methylenes which constitute Z may be replaced by any one of a phenylene and an —O—;

(2) the compounds described in (1) above, in which n is 1;

(3) the compounds described in (2) above, in which Z is a straight chain alkyl group having 2 to 10 carbon atoms, a straight chain alkyl group having 2 to 10 carbon atoms with one of methylenes which constitute Z being replaced by a phenylene, a straight chain alkyl group having 2 to 10 carbon atoms with one of methylenes which constitute Z being replaced by an —O—, or a straight chain alkyl group having 2 to 10 carbon atoms with one of methylenes which constitute Z being replaced by a phenylene and another methylene being replaced by —O—;

(4) the compounds described in (3) above, in which Z is a straight chain methylene group having from 2 to 10 carbon atoms, a straight chain methylene group having from 2 to 10 carbon atoms with one of methylenes thereof being replaced by a phenylene, a straight chain methylene group having from 2 to 10 carbon atoms with one of methylenes thereof being replaced by an —O—, or a straight chain methylene group having from 2 to 10 carbon atoms with one of methylenes thereof being replaced by a phenylene and another being replaced by an —O—;

(5) the compounds described in (4) above, in which Z is a straight chain methylene group having from 2 to 10 carbon atoms;

(6) the compounds described in (4) or (5) above, in which Y is —NHCS — or NHCSNH — at the para—position or meta—position;

(7) the compounds described in (6) above, in which Y is —NHCSNH—at the meta—position and Z is a straight chain methylene group having from 2 to 10 carbon atoms;

(8) the compounds described in (6) above, in which Y is —NHCS— at the meta—position and Z is a straight chain methylene group having from 2 to 10 carbon atoms;

(9) the compounds described in (8) above, in which Y is —NHCS— at the meta—position and Z is a straight chain methylene group having 5 carbon atoms;

(10) the compounds described in (4) above, in which Y is —NHCSNH— at the meta-position and Z is a straight chain methylene group having from 2 to 10 carbon atoms with one of methylenes thereof being replaced by a phenylene;

(11) the compounds described in (6) above, in which Y is —NHCS— or —NHCSNH— at the meta-position and Z is represented by formula (sp-4) below

[wherein *a is bonded to a bond with Y in the formula (1) and *b is bonded to a bond with N⁺R⁵R⁶R⁷];

(12) the compounds described in (10) or (11) above, in which Y is —NHCSNH— at the meta-position;

(13) the compounds described in any one of (1) to (12) above, in which the N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent:

I) R⁵, R⁶, and R⁷, which may be mutually different, each represents any one of an alkyl group having from 1 to 10 carbon atoms, an alkenyl group having from 3 to 8 carbon atoms, and an alkynyl group having from 3 to 9 carbon atoms, where the alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a thienyl group, a cyclohexyl group, a cyano group, a hydroxyl group, an oxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group, and further, at least one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a thienylene, a furylene, an —O—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰— in which R5 represents an alkyl group having from 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms and the alkyl group may be substituted with at least one of a phenyl group and a hydroxyl group; R⁹ and R¹⁰ which may be mutually different, each represents an alkyl group having from 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms and the alkyl group may be substituted with at least one of a phenyl group and a hydroxyl group,

II) N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring which is any one of a pyrrolidinium ring, a piperidinium ring, a morpholinium ring, a thiomorpholinium ring, a piperazinium ring, an azepanium ring, a quinuclidinium ring, or a 1 ,4-diazabicyclo[2.2.2]octanium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a cyano group, a phenyl group, a —CON H₂ group, and an —R¹¹ group; R¹¹ represents an alkyl group having from 1 to 6 carbon atoms or an alkenyl group having 3 carbon atoms, where the alkyl group represented by R¹¹ may be substituted with at least one of a hydroxyl group, a cyano group, a phenyl group, and a —CONH₂ group; moreover, at least one of methylenes which constitute the alkyl group may be replaced by any one of an —O—, a —CO₂—, and an —NHCO—; among R⁵, R⁶, and R⁷, a group which is not involved in formation of the ring represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, or an alkynyl group having 3 to 6 carbon atoms; the alkyl group, the alkenyl group, and the alkynyl group represented by R⁵, R⁶, or R⁷ may be substituted with at least one of a phenyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cyclopropyl group, a cyclopentyl group, a cyano group, a hydroxyl group, an oxo group, a nitro group, a carboxyl group, an CONH₂ group, and an SO₃H group; and moreover, at least one of methylenes which constitute the alkyl group may be replaced by any one of a phenylene, an —O—, and a —CO₂—,

III) N⁺R⁵R⁶R⁷ represents a pyridinium ring, a quinolinium ring, or an isoquinolinium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the pyridinium ring and the quinolinium ring may be substituted with at least one of a cyano group, a nitro group, a phenyl group, a thienyl group, a pyridyl group, an alkoxy group having from 1 to 3 carbon atoms, a carboxyl group, a —CONH₂ group, and an —R¹² group; R¹² represents an alkyl group having from 1 to 9 carbon atoms or an alkenyl group having from 2 to 4 carbon atoms; and the alkyl group and the alkenyl group represented by R¹² may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a cyano group, a nitro group, a hydroxyl group, an oxo group, a carboxyl group, and an —SO₃H group; and further, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of an —S— , a —CO₂—, an —NHCO— , and an —NR⁸— where R⁸ represents an alkyl group having 1 to 3 carbon atoms and the alkyl group may be substituted with at least one hydroxyl group;

(14) the compounds described in any one of (1) to (13), in which the N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent;

I) R⁵, R⁶, and R⁷, which may be mutually different, each represents an alkyl group having from 1 to 10 carbon atoms, a straight chain alkenyl group having from 3 to 6 or 8 carbon atoms, a branched alkenyl group having 4, 6 or 7 carbon atoms, a straight chain alkynyl group having from 3, 5, 6, 7 or 9 carbon atoms, or a branched alkynyl group having 6 carbon atoms, in which 1) the preferable alkyl group, alkenyl group, and alkynyl group represented by R⁵, R⁶, and R⁷ are substituted with any one of a phenyl group, a thienyl group, a cyclohexyl group, a cyano group, a hydroxyl group, an oxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group, 2) the alkyl group, the alkenyl group, and the alkynyl group are substituted with two hydroxyl groups, 3) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group and one —SO₃H group, 4) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one oxo group and one phenyl group, 5) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group and two phenyl groups, 6) one of methylenes which constitutes the alkyl group, the alkenyl group, and the alkynyl group is replaced by any one of a phenylene, a furylene, a —CO₂—, an —NHCO—, an —NR⁸— (where R⁸ represents a methyl group, an ethyl group, an n-propyl group, a 2-propenyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, or a benzyl group), and an —N⁺W⁻R⁹R¹⁰— (where R⁹ and R¹⁰ each represents a methyl group, an ethyl group, an n-propyl group, a 2-propenyl group, a 2-hydroxyethyl group, or a benzyl group), 7) two of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group are replaced by any one selected from two (—O—)s, one phenylene and one —O—, one —O— and one —NR⁸—, and one —NHCO— and one —O—, 8) three of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group are replaced by any one selected from two (—O—)s and one or one phenylene and two (—NHCO—)s, 9) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by an —O—, 10) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by an —NR⁸—, 11) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group, and moreover one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by a furylene, 12) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one oxo group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by a thienylene, 13) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one oxo group, and moreover, two of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group are replaced by one —O— and one phenylene, or the alkyl group, alkenyl group, and alkynyl group are neither substituted nor replaced,

II) N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring which is any one of a pyrrolidinium ring, a piperidinium ring, a morpholinium ring, a thiomorpholinium ring, a piperazinium ring, an azepanium ring, a quinuclidinium ring, and a 1,4-diazabicyclo[2.2.2]octanium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the monocyclic ring and the bicyclic ring are 1) substituted with any one of a hydroxyl group, an oxo group, a cyano group, a phenyl group, a —CONH₂ group, and an —R¹¹ group, 2) substituted with one cyano group and one hydroxyl group, 3) substituted with one hydroxyl group and one —R¹¹, 4) substituted with one oxo group and one —R¹¹,5) substituted with two oxo groups, or 6) substituted with two (—R¹¹)s, or the monocyclic ring and the bicyclic ring are unsubstituted, where R¹¹ represents any one of a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-propenyl group, a benzyl group, an acetylamino group, a t-butoxycarbonylamino group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-cyanoethoxy group, a (2-cyanoethoxy)methyl group, a 2-carbamoylethoxy group, an ethoxycarbonyl group, a t-butoxycarbonyl group, a benzoyloxy group, a phenylacetylamino group, a butanoylamino group, and a pentanoylamino group;

Among R⁵, R⁶, and R⁷, a group which is not involved in the formation of the ring represents a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkenyl group having from 3 to 4 carbon atoms, or a straight chain alkynyl group having 3, 4, or 6 carbon atoms, in which 1) the alkyl group, the alkenyl group, and the alkynyl group represented by R⁵, R⁶, or R⁷ are substituted with any one of a phenyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cyclopropyl group, a cyclopentyl group, a cyano group, a hydroxyl group, a carboxyl group, and an —SO₃H group, 2) the alkyl group, the alkenyl group, and the alkynyl group are substituted with two hydroxyl groups, 3) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group and one —SO₃H, 4) the alkyl group, the alkenyl group, and the alkynyl group are substituted with four hydroxyl groups and one oxo group, 5) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one nitro group and one morpholyl group, 6) one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by a —CO₂—, or 7) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one morpholyl group and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by an —O—, or the alkyl group, the alkenyl group, and the alkynyl group are neither substituted nor replaced,

III) N⁺R⁵R⁶R⁷ represents any one of 1) a pyridinium ring substituted with any one of a cyano group, a phenyl group, a thienyl group, a pyridyl group, a methoxy group, an ethoxy group, a propoxy group, a carboxyl group, a —CONH₂— group, and a —R¹² group, 2) a pyridinium ring substituted with two cyano groups, 3) a pyridinium group substituted with two (—R¹²)s, 4) a pyridinium ring substituted with one cyano group and one —R¹², 5) a pyridinium ring substituted with one phenyl group and one —R¹², 6) a quinolinium ring substituted with any one of a cyano group, a nitro group, a carboxyl group, a methoxy group, an ethoxy group, a propoxy group, and —R¹², 7) a quinolinium ring substituted with one methoxy group and one —R¹², 8) a quinolinium ring substituted with one nitro group and one —R¹², 9) an unsubstituted pyridinium ring, 10) an unsubstituted quinolinium ring, or 11) an unsubstituted isoquinolinium ring, where R¹² represents any one of a methyl group, an ethyl group, an n—propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a 3-pentyl group, a 5-nonyl group, a vinyl group, a benzyl group, a 3-phenylpropyl group, a 2-(1-naphthyl)vinyl group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a formyl group, an acetyl group, a propionyl group, a benzoyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, a hexoxycarbonyl group, a benzyloxycarbonyl group, a 2-propenyloxycarbonyl group, an ethoxycarbonylmethyl group, a 2-(methoxycarbonyl)ethyl group, an ethoxycarbonylmethylcarbonyl group, a 2-hydroxyethylaminocarbonyl group, a bis(2-hydroxyethyl)aminocarbonyl group, a 2-carboxyvinyl group, a carboxymethylthio group, a cyanomethyl group, a 2-nitrovinyl group, a 2-(4-pyridyl)ethyl group, a 2-(4-pyridyl)vinyl group, a 3-(4-pyridyl)propyl group, a 2-(4-pyridyl)-1,2-dihydroxyethyl group, and a 2-sulfoethyl group, provided that the position of its bonding with Z is an ammonium nitrogen atom;

(15) the compounds described in any one of (1) to (14), in which the N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent;

I) R⁵, R⁶, and R⁷, which may be mutually different, each represents any one of a straight chain alkyl group having from 1 to 10 carbon atoms, a straight chain alkyl group having from 1 to 10 carbon atoms which is substituted with one phenyl group, a straight chain alkyl group having from 1 to 10 carbon atoms which is substituted with one hydroxyl group, an alkenyl group having from 3 to 6, or 8 carbon atoms, a branched alkenyl group having 4, 6, or 7 carbon atoms, a straight chain alkynyl group having 3, 5, 6, 7, or 9 carbon atoms, and a branched alkynyl group having 6 carbon atoms,

II) N⁺R⁵R⁶R⁷ represents a pyrrolidinium ring, a piperidinium ring, an azepanium ring, a quinuclidinium ring, or a 1,4-diazabicyclo[2 22]- octanium ring, substituted with any one of a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-propenyl group, a benzyl group, a hydroxyl group, a hydroxyl group, a hydroxymethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group, or unsubstituted,

provided that the position of its bonding with Z is an ammonium nitrogen atom; among R⁵, R⁶, and R⁷, any group that is not involved in the formation of the ring represents any one of a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkyl group having from 1 to 6 carbon atoms which is substituted with one phenyl group, a straight chain alkyl group having from 1 to 6 carbon atoms which is substituted with one hydroxyl group, a straight chain alkenyl group having from 3 to 4 carbon atoms, and a straight chain alkynyl group having 3, 4, or 6 carbon atoms,

III) N⁺R⁵R⁶R⁷ represents an unsubstituted pyridinium ring, an unsubstituted quinolinium ring, an unsubstituted isoquinolinium ring, a pyridinium ring substituted with any one of a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a vinyl group, a phenyl group, a benzyl group, a 3-phenylpropyl group, a hydroxymethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group, a pyridinium ring substituted with any two of a methyl group and an ethyl group, a pyridinium ring substituted with one phenyl group and one methyl group, and a quinolinium ring substituted with any one of a methyl group and an -propyl group, provided that the position of its bonding with Z is ammonium nitrogen atom.

(16) the compounds described in any one of (13) to (15), in which R1 and R², which may be mutually different, each represents a straight chain alkyl group having 2 to 6 carbon atoms, and (NR³R⁴)_(m) represents any one of a dimethylamino group substituting at the 7-position, a diethylamino group substituting at the 7-position, an ethylmethylamino group substituting at the 7-position, a dimethylamino group substituting at the 9-position, and dimethylamino groups substituting at the 7- and 9-positions;

(17) the compounds described in (16) above, in which (NR³R⁴)_(m) is any one of a dimethylamino group substituting at the 7-position, a diethylamino group substituting at the 7-position, and an ethylmethylamino group substituting at the 7-position, and N⁺R⁵R⁶R⁷ is any one of a 4-t-butylpyridinium group, a 3-(3-hydroxypropyl)-pyridinium group, a 3-[2-(methoxycarbonyl)ethyl]-pyridinium group, a 2-(n-propyl)-pyridinium group, a 4-phenylquinuclidinium group, and a 1,4-diazabicyclo[2.2.2]octanium group; and (18) the compounds described in (17), in which both R1 and R2 are n-butyl groups, and (NR³R⁴)_(m) is a dimethylamino group substituting at the 7-position.

In the compounds of the present invention, asymmetric centers can exist also in Z and (N⁺R⁵R⁶R⁷) in addition to the 3-position and the 5-position in the formula (1), so that there can be a plurality of stereo isomers depending on the number of asymmetric centers. Not only pure stereoisomers but also mixtures of any plural number of isomers are included in the scope of the present invention. Moreover, there can exist a plurality of geometrical isomers depending on the types of Z and (N⁺R⁵R⁶R⁷) in the compounds of the present invention. Not only pure geometrical isomers but also mixtures of any plural number of the isomers are included in the scope of the present invention.

Further, the present invention provides pharmaceutical compositions which contain the compounds of the present invention as active ingredients; a pharmaceutical composition which is a cholesterol-lowering agent, a pharmaceutical composition which is a therapeutic or preventive agent for any one of hyperlipidemia, arteriosclerosis, and syndrome X, a pharmaceutical composition which is a treating or preventing agent for cholestasis-caused hepatopathy, a pharmaceutical composition which is a treating or preventing agent for any one of primary biliary cirrhosis and primary sclerosing cholangitis, a pharmaceutical composition which is a treating or preventing agent for obesity and fatty liver, and a pharmaceutical composition which is a treating or preventing agent for steatohepatitis.

Due to their characteristic of having a thioamide bond in the molecule, the compounds of the present invention can be fully expected to act as radical scavengers. Radicals have high cytotoxicities; for example, when they act on alimentary canal, they are considered to cause alimentary canal disorder, for example, inflammatory enteritis (see Thomson A et al., Dig Dis, 16: 152-158, 1998). Furthermore, thiourea has been reported to have a protective effect against disorder of amino acid transporter (that is, inhibition of amino acid absorption) in small intestine caused by hydroxy radical and to be useful as a radical scavenger (see Hayashi K. et al., Scand. J. Gastroenterol, 28, 261-266, 1993). Taking this into consideration, the compounds of the present invention are considered to have an effect as a radical scavenger which can be used in the treatment or prevention of the disorder of alimentary canal, for example, inflammatory enteritis. A method for examining the radical scavenging effect includes a method of mixing the compound of the present invention with a compound which generates a hydroxy radical, for example, a hydrogen peroxide solution, t-BuOOH or the like and measuring the remaining quantity of radical using a physicochemical or a biochemical method. Moreover, the method for examining the radical scavenging effect includes a method of allowing the compound of the present invention to coexist in a model of causing disorder in a tissue of small intestine or small intestine epithelial cell line with a compound which generates a hydroxy radical, and an effect of decreasing the degree of disorder is examined. Note that the method of Hayashi et al. (see Hayashi K. et al., Scand. J. Gastroenterol, 28, 262-266, 1993) may be exemplified as a more specific method.

The 1,4-benzothiazepine skeleton, which is the basic skeleton of the compounds of the present invention, has a basic nitrogen at the 4-position which is a position adjacent to the center of asymmetry, so that optical isomers can be readily acquired by using various optical resolving agents such as camphor-sulfonic acid derivatives and tartaric acid derivatives. Moreover, since the 1,4-benzothiazepine skeleton forms pharmaceutically acceptable salts with various acids due to the existence of the basic nitrogen therein, compounds having acceptable water solubilities can be acquired, so that the skeleton is a basic skeleton which is useful for producing pharmaceuticals. The compounds of the present invention, which include the skeleton and a thioamide bond and a quaternary ammonium substituent introduced therein, are novel compounds which exhibit a very potent ileal bile acid transportation inhibiting activity and have stability in that the compounds are less susceptible to metabolism in vivo and have a reduced toxicity to the alimentary canal. The test examples described above have verified that the compounds of the present invention are useful as cholesterol-lowering agents, and furthermore they are useful for use in pharmaceutical compositions for treating or preventing hyperlipidemia, arteriosclerosis, syndrome X and the like. Also, it has been verified that the compounds of the present invention are useful as agents for ameliorating cholestasis-caused hepatopathy, and furthermore it has been verified that they are useful for use in pharmaceutical compositions for the treatment and prevention of cholestasis-caused hepatopathy, for example, primary biliary cirrhosis or primary sclerosing cholangitis. Further, it has been verified that the compounds of the present invention are useful for use in pharmaceutical compositions for the treatment and prevention of obesity and fatty liver. Moreover, it has been verified that the compounds of the present invention are useful for use in pharmaceutical compositions for treating and preventing steatohepatitis. In addition, it has been verified that the pharmaceutical compositions which contain ileal bile acid transporter inhibiting compounds as active ingredients are effective on cholestasis-caused hepatopathy and are useful for use in pharmaceutical compositions for the treatment and prevention of, in particular, primary biliary cirrhosis or primary sclerosing cholangitis.

The other objects, features and advantages of the present invention are specifically set forth in or will become apparent from the following detailed descriptions of the invention.

DETAILED DESCRIPTION

Specific examples of the compound represented by formula (1) include the following compounds and acid addition salts thereof.

Compounds in which both R¹ and R² are butyl groups, NR³R⁴ is a 7-dimethylamino group, X⁻ is Br⁻, and the bonding position of Y is the meta-position include those compounds described in Table 1 (from 1A0001 to 1A6681, from 1U0001 to 1U6681, and from 1C0001 to 1C3930). From (sp-1) to (sp-25) and from (an-1) to (an-393) in Table 1, are as mentioned earlier.

TABLE 1 Y = NHCS Y = NHCSNH Y = NHCSO Exempli- Exempli- Exempli- fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ 1A0001 sp-1 an-1 1U0001 sp-1 an-1 1C0001 sp-1 an-1 1A0002 sp-1 an-2 1U0002 sp-1 an-2 1C0002 sp-1 an-2 1A0003 sp-1 an-3 1U0003 sp-1 an-3 1C0003 sp-1 an-3 1A0004 sp-1 an-4 1U0004 sp-1 an-4 1C0004 sp-1 an-4 1A0005 sp-1 an-5 1U0005 sp-1 an-5 1C0005 sp-1 an-5 1A0006 sp-1 an-6 1U0006 sp-1 an-6 1C0006 sp-1 an-6 1A0007 sp-1 an-7 1U0007 sp-1 an-7 1C0007 sp-1 an-7 1A0008 sp-1 an-8 1U0008 sp-1 an-8 1C0008 sp-1 an-8 1A0009 sp-1 an-9 1U0009 sp-1 an-9 1C0009 sp-1 an-9 1A0010 sp-1 an-10 1U0010 sp-1 an-10 1C0010 sp-1 an-10 1A0011 sp-1 an-11 1U0011 sp-1 an-11 1C0011 sp-1 an-11 1A0012 sp-1 an-12 1U0012 sp-1 an-12 1C0012 sp-1 an-12 1A0013 sp-1 an-13 1U0013 sp-1 an-13 1C0013 sp-1 an-13 1A0014 sp-1 an-14 1U0014 sp-1 an-14 1C0014 sp-1 an-14 1A0015 sp-1 an-15 1U0015 sp-1 an-15 1C0015 sp-1 an-15 1A0016 sp-1 an-16 1U0016 sp-1 an-16 1C0016 sp-1 an-16 1A0017 sp-1 an-17 1U0017 sp-1 an-17 1C0017 sp-1 an-17 1A0018 sp-1 an-18 1U0018 sp-1 an-18 1C0018 sp-1 an-18 1A0019 sp-1 an-19 1U0019 sp-1 an-19 1C0019 sp-1 an-19 1A0020 sp-1 an-20 1U0020 sp-1 an-20 1C0020 sp-1 an-20 1A0021 sp-1 an-21 1U0021 sp-1 an-21 1C0021 sp-1 an-21 1A0022 sp-1 an-22 1U0022 sp-1 an-22 1C0022 sp-1 an-22 1A0023 sp-1 an-23 1U0023 sp-1 an-23 1C0023 sp-1 an-23 1A0024 sp-1 an-24 1U0024 sp-1 an-24 1C0024 sp-1 an-24 1A0025 sp-1 an-25 1U0025 sp-1 an-25 1C0025 sp-1 an-25 1A0026 sp-1 an-26 1U0026 sp-1 an-26 1C0026 sp-1 an-26 1A0027 sp-1 an-27 1U0027 sp-1 an-27 1C0027 sp-1 an-27 1A0028 sp-1 an-28 1U0028 sp-1 an-28 1C0028 sp-1 an-28 1A0029 sp-1 an-29 1U0029 sp-1 an-29 1C0029 sp-1 an-29 1A0030 sp-1 an-30 1U0030 sp-1 an-30 1C0030 sp-1 an-30 1A0031 sp-1 an-31 1U0031 sp-1 an-31 1C0031 sp-1 an-31 1A0032 sp-1 an-32 1U0032 sp-1 an-32 1C0032 sp-1 an-32 1A0033 sp-1 an-33 1U0033 sp-1 an-33 1C0033 sp-1 an-33 1A0034 sp-1 an-34 1U0034 sp-1 an-34 1C0034 sp-1 an-34 1A0035 sp-1 an-35 1U0035 sp-1 an-35 1C0035 sp-1 an-35 1A0036 sp-1 an-36 1U0036 sp-1 an-36 1C0036 sp-1 an-36 1A0037 sp-1 an-37 1U0037 sp-1 an-37 1C0037 sp-1 an-37 1A0038 sp-1 an-38 1U0038 sp-1 an-38 1C0038 sp-1 an-38 1A0039 sp-1 an-39 1U0039 sp-1 an-39 1C0039 sp-1 an-39 1A0040 sp-1 an-40 1U0040 sp-1 an-40 1C0040 sp-1 an-40 1A0041 sp-1 an-41 1U0041 sp-1 an-41 1C0041 sp-1 an-41 1A0042 sp-1 an-42 1U0042 sp-1 an-42 1C0042 sp-1 an-42 1A0043 sp-1 an-43 1U0043 sp-1 an-43 1C0043 sp-1 an-43 1A0044 sp-1 an-44 1U0044 sp-1 an-44 1C0044 sp-1 an-44 1A0045 sp-1 an-45 1U0045 sp-1 an-45 1C0045 sp-1 an-45 1A0046 sp-1 an-46 1U0046 sp-1 an-46 1C0046 sp-1 an-46 1A0047 sp-1 an-47 1U0047 sp-1 an-47 1C0047 sp-1 an-47 1A0048 sp-1 an-48 1U0048 sp-1 an-48 1C0048 sp-1 an-48 1A0049 sp-1 an-49 1U0049 sp-1 an-49 1C0049 sp-1 an-49 1A0050 sp-1 an-50 1U0050 sp-1 an-50 1C0050 sp-1 an-50 1A0051 sp-1 an-51 1U0051 sp-1 an-51 1C0051 sp-1 an-51 1A0052 sp-1 an-52 1U0052 sp-1 an-52 1C0052 sp-1 an-52 1A0053 sp-1 an-53 1U0053 sp-1 an-53 1C0053 sp-1 an-53 1A0054 sp-1 an-54 1U0054 sp-1 an-54 1C0054 sp-1 an-54 1A0055 sp-1 an-55 1U0055 sp-1 an-55 1C0055 sp-1 an-55 1A0056 sp-1 an-56 1U0056 sp-1 an-56 1C0056 sp-1 an-56 1A0057 sp-1 an-57 1U0057 sp-1 an-57 1C0057 sp-1 an-57 1A0058 sp-1 an-58 1U0058 sp-1 an-58 1C0058 sp-1 an-58 1A0059 sp-1 an-59 1U0059 sp-1 an-59 1C0059 sp-1 an-59 1A0060 sp-1 an-60 1U0060 sp-1 an-60 1C0060 sp-1 an-60 1A0061 sp-1 an-61 1U0061 sp-1 an-61 1C0061 sp-1 an-61 1A0062 sp-1 an-62 1U0062 sp-1 an-62 1C0062 sp-1 an-62 1A0063 sp-1 an-63 1U0063 sp-1 an-63 1C0063 sp-1 an-63 1A0064 sp-1 an-64 1U0064 sp-1 an-64 1C0064 sp-1 an-64 1A0065 sp-1 an-65 1U0065 sp-1 an-65 1C0065 sp-1 an-65 1A0066 sp-1 an-66 1U0066 sp-1 an-66 1C0066 sp-1 an-66 1A0067 sp-1 an-67 1U0067 sp-1 an-67 1C0067 sp-1 an-67 1A0068 sp-1 an-68 1U0068 sp-1 an-68 1C0068 sp-1 an-68 1A0069 sp-1 an-69 1U0069 sp-1 an-69 1C0069 sp-1 an-69 1A0070 sp-1 an-70 1U0070 sp-1 an-70 1C0070 sp-1 an-70 1A0071 sp-1 an-71 1U0071 sp-1 an-71 1C0071 sp-1 an-71 1A0072 sp-1 an-72 1U0072 sp-1 an-72 1C0072 sp-1 an-72 1A0073 sp-1 an-73 1U0073 sp-1 an-73 1C0073 sp-1 an-73 1A0074 sp-1 an-74 1U0074 sp-1 an-74 1C0074 sp-1 an-74 1A0075 sp-1 an-75 1U0075 sp-1 an-75 1C0075 sp-1 an-75 1A0076 sp-1 an-76 1U0076 sp-1 an-76 1C0076 sp-1 an-76 1A0077 sp-1 an-77 1U0077 sp-1 an-77 1C0077 sp-1 an-77 1A0078 sp-1 an-78 1U0078 sp-1 an-78 1C0078 sp-1 an-78 1A0079 sp-1 an-79 1U0079 sp-1 an-79 1C0079 sp-1 an-79 1A0080 sp-1 an-80 1U0080 sp-1 an-80 1C0080 sp-1 an-80 1A0081 sp-1 an-81 1U0081 sp-1 an-81 1C0081 sp-1 an-81 1A0082 sp-1 an-82 1U0082 sp-1 an-82 1C0082 sp-1 an-82 1A0083 sp-1 an-83 1U0083 sp-1 an-83 1C0083 sp-1 an-83 1A0084 sp-1 an-84 1U0084 sp-1 an-84 1C0084 sp-1 an-84 1A0085 sp-1 an-85 1U0085 sp-1 an-85 1C0085 sp-1 an-85 1A0086 sp-1 an-86 1U0086 sp-1 an-86 1C0086 sp-1 an-86 1A0087 sp-1 an-87 1U0087 sp-1 an-87 1C0087 sp-1 an-87 1A0088 sp-1 an-88 1U0088 sp-1 an-88 1C0088 sp-1 an-88 1A0089 sp-1 an-89 1U0089 sp-1 an-89 1C0089 sp-1 an-89 1A0090 sp-1 an-90 1U0090 sp-1 an-90 1C0090 sp-1 an-90 1A0091 sp-1 an-91 1U0091 sp-1 an-91 1C0091 sp-1 an-91 1A0092 sp-1 an-92 1U0092 sp-1 an-92 1C0092 sp-1 an-92 1A0093 sp-1 an-93 1U0093 sp-1 an-93 1C0093 sp-1 an-93 1A0094 sp-1 an-94 1U0094 sp-1 an-94 1C0094 sp-1 an-94 1A0095 sp-1 an-95 1U0095 sp-1 an-95 1C0095 sp-1 an-95 1A0096 sp-1 an-96 1U0096 sp-1 an-96 1C0096 sp-1 an-96 1A0097 sp-1 an-97 1U0097 sp-1 an-97 1C0097 sp-1 an-97 1A0098 sp-1 an-98 1U0098 sp-1 an-98 1C0098 sp-1 an-98 1A0099 sp-1 an-99 1U0099 sp-1 an-99 1C0099 sp-1 an-99 1A0100 sp-1 an-100 1U0100 sp-1 an-100 1C0100 sp-1 an-100 1A0101 sp-1 an-101 1U0101 sp-1 an-101 1C0101 sp-1 an-101 1A0102 sp-1 an-102 1U0102 sp-1 an-102 1C0102 sp-1 an-102 1A0103 sp-1 an-103 1U0103 sp-1 an-103 1C0103 sp-1 an-103 1A0104 sp-1 an-104 1U0104 sp-1 an-104 1C0104 sp-1 an-104 1A0105 sp-1 an-105 1U0105 sp-1 an-105 1C0105 sp-1 an-105 1A0106 sp-1 an-106 1U0106 sp-1 an-106 1C0106 sp-1 an-106 1A0107 sp-1 an-107 1U0107 sp-1 an-107 1C0107 sp-1 an-107 1A0108 sp-1 an-108 1U0108 sp-1 an-108 1C0108 sp-1 an-108 1A0109 sp-1 an-109 1U0109 sp-1 an-109 1C0109 sp-1 an-109 1A0110 sp-1 an-110 1U0110 sp-1 an-110 1C0110 sp-1 an-110 1A0111 sp-1 an-111 1U0111 sp-1 an-111 1C0111 sp-1 an-111 1A0112 sp-1 an-112 1U0112 sp-1 an-112 1C0112 sp-1 an-112 1A0113 sp-1 an-113 1U0113 sp-1 an-113 1C0113 sp-1 an-113 1A0114 sp-1 an-114 1U0114 sp-1 an-114 1C0114 sp-1 an-114 1A0115 sp-1 an-115 1U0115 sp-1 an-115 1C0115 sp-1 an-115 1A0116 sp-1 an-116 1U0116 sp-1 an-116 1C0116 sp-1 an-116 1A0117 sp-1 an-117 1U0117 sp-1 an-117 1C0117 sp-1 an-117 1A0118 sp-1 an-118 1U0118 sp-1 an-118 1C0118 sp-1 an-118 1A0119 sp-1 an-119 1U0119 sp-1 an-119 1C0119 sp-1 an-119 1A0120 sp-1 an-120 1U0120 sp-1 an-120 1C0120 sp-1 an-120 1A0121 sp-1 an-121 1U0121 sp-1 an-121 1C0121 sp-1 an-121 1A0122 sp-1 an-122 1U0122 sp-1 an-122 1C0122 sp-1 an-122 1A0123 sp-1 an-123 1U0123 sp-1 an-123 1C0123 sp-1 an-123 1A0124 sp-1 an-124 1U0124 sp-1 an-124 1C0124 sp-1 an-124 1A0125 sp-1 an-125 1U0125 sp-1 an-125 1C0125 sp-1 an-125 1A0126 sp-1 an-126 1U0126 sp-1 an-126 1C0126 sp-1 an-126 1A0127 sp-1 an-127 1U0127 sp-1 an-127 1C0127 sp-1 an-127 1A0128 sp-1 an-128 1U0128 sp-1 an-128 1C0128 sp-1 an-128 1A0129 sp-1 an-129 1U0129 sp-1 an-129 1C0129 sp-1 an-129 1A0130 sp-1 an-130 1U0130 sp-1 an-130 1C0130 sp-1 an-130 1A0131 sp-1 an-131 1U0131 sp-1 an-131 1C0131 sp-1 an-131 1A0132 sp-1 an-132 1U0132 sp-1 an-132 1C0132 sp-1 an-132 1A0133 sp-1 an-133 1U0133 sp-1 an-133 1C0133 sp-1 an-133 1A0134 sp-1 an-134 1U0134 sp-1 an-134 1C0134 sp-1 an-134 1A0135 sp-1 an-135 1U0135 sp-1 an-135 1C0135 sp-1 an-135 1A0136 sp-1 an-136 1U0136 sp-1 an-136 1C0136 sp-1 an-136 1A0137 sp-1 an-137 1U0137 sp-1 an-137 1C0137 sp-1 an-137 1A0138 sp-1 an-138 1U0138 sp-1 an-138 1C0138 sp-1 an-138 1A0139 sp-1 an-139 1U0139 sp-1 an-139 1C0139 sp-1 an-139 1A0140 sp-1 an-140 1U0140 sp-1 an-140 1C0140 sp-1 an-140 1A0141 sp-1 an-141 1U0141 sp-1 an-141 1C0141 sp-1 an-141 1A0142 sp-1 an-142 1U0142 sp-1 an-142 1C0142 sp-1 an-142 1A0143 sp-1 an-143 1U0143 sp-1 an-143 1C0143 sp-1 an-143 1A0144 sp-1 an-144 1U0144 sp-1 an-144 1C0144 sp-1 an-144 1A0145 sp-1 an-145 1U0145 sp-1 an-145 1C0145 sp-1 an-145 1A0146 sp-1 an-146 1U0146 sp-1 an-146 1C0146 sp-1 an-146 1A0147 sp-1 an-147 1U0147 sp-1 an-147 1C0147 sp-1 an-147 1A0148 sp-1 an-148 1U0148 sp-1 an-148 1C0148 sp-1 an-148 1A0149 sp-1 an-149 1U0149 sp-1 an-149 1C0149 sp-1 an-149 1A0150 sp-1 an-150 1U0150 sp-1 an-150 1C0150 sp-1 an-150 1A0151 sp-1 an-151 1U0151 sp-1 an-151 1C0151 sp-1 an-151 1A0152 sp-1 an-152 1U0152 sp-1 an-152 1C0152 sp-1 an-152 1A0153 sp-1 an-153 1U0153 sp-1 an-153 1C0153 sp-1 an-153 1A0154 sp-1 an-154 1U0154 sp-1 an-154 1C0154 sp-1 an-154 1A0155 sp-1 an-155 1U0155 sp-1 an-155 1C0155 sp-1 an-155 1A0156 sp-1 an-156 1U0156 sp-1 an-156 1C0156 sp-1 an-156 1A0157 sp-1 an-157 1U0157 sp-1 an-157 1C0157 sp-1 an-157 1A0158 sp-1 an-158 1U0158 sp-1 an-158 1C0158 sp-1 an-158 1A0159 sp-1 an-159 1U0159 sp-1 an-159 1C0159 sp-1 an-159 1A0160 sp-1 an-160 1U0160 sp-1 an-160 1C0160 sp-1 an-160 1A0161 sp-1 an-161 1U0161 sp-1 an-161 1C0161 sp-1 an-161 1A0162 sp-1 an-162 1U0162 sp-1 an-162 1C0162 sp-1 an-162 1A0163 sp-1 an-163 1U0163 sp-1 an-163 1C0163 sp-1 an-163 1A0164 sp-1 an-164 1U0164 sp-1 an-164 1C0164 sp-1 an-164 1A0165 sp-1 an-165 1U0165 sp-1 an-165 1C0165 sp-1 an-165 1A0166 sp-1 an-166 1U0166 sp-1 an-166 1C0166 sp-1 an-166 1A0167 sp-1 an-167 1U0167 sp-1 an-167 1C0167 sp-1 an-167 1A0168 sp-1 an-168 1U0168 sp-1 an-168 1C0168 sp-1 an-168 1A0169 sp-1 an-169 1U0169 sp-1 an-169 1C0169 sp-1 an-169 1A0170 sp-1 an-170 1U0170 sp-1 an-170 1C0170 sp-1 an-170 1A0171 sp-1 an-171 1U0171 sp-1 an-171 1C0171 sp-1 an-171 1A0172 sp-1 an-172 1U0172 sp-1 an-172 1C0172 sp-1 an-172 1A0173 sp-1 an-173 1U0173 sp-1 an-173 1C0173 sp-1 an-173 1A0174 sp-1 an-174 1U0174 sp-1 an-174 1C0174 sp-1 an-174 1A0175 sp-1 an-175 1U0175 sp-1 an-175 1C0175 sp-1 an-175 1A0176 sp-1 an-176 1U0176 sp-1 an-176 1C0176 sp-1 an-176 1A0177 sp-1 an-177 1U0177 sp-1 an-177 1C0177 sp-1 an-177 1A0178 sp-1 an-178 1U0178 sp-1 an-178 1C0178 sp-1 an-178 1A0179 sp-1 an-179 1U0179 sp-1 an-179 1C0179 sp-1 an-179 1A0180 sp-1 an-180 1U0180 sp-1 an-180 1C0180 sp-1 an-180 1A0181 sp-1 an-181 1U0181 sp-1 an-181 1C0181 sp-1 an-181 1A0182 sp-1 an-182 1U0182 sp-1 an-182 1C0182 sp-1 an-182 1A0183 sp-1 an-183 1U0183 sp-1 an-183 1C0183 sp-1 an-183 1A0184 sp-1 an-184 1U0184 sp-1 an-184 1C0184 sp-1 an-184 1A0185 sp-1 an-185 1U0185 sp-1 an-185 1C0185 sp-1 an-185 1A0186 sp-1 an-186 1U0186 sp-1 an-186 1C0186 sp-1 an-186 1A0187 sp-1 an-187 1U0187 sp-1 an-187 1C0187 sp-1 an-187 1A0188 sp-1 an-188 1U0188 sp-1 an-188 1C0188 sp-1 an-188 1A0189 sp-1 an-189 1U0189 sp-1 an-189 1C0189 sp-1 an-189 1A0190 sp-1 an-190 1U0190 sp-1 an-190 1C0190 sp-1 an-190 1A0191 sp-1 an-191 1U0191 sp-1 an-191 1C0191 sp-1 an-191 1A0192 sp-1 an-192 1U0192 sp-1 an-192 1C0192 sp-1 an-192 1A0193 sp-1 an-193 1U0193 sp-1 an-193 1C0193 sp-1 an-193 1A0194 sp-1 an-194 1U0194 sp-1 an-194 1C0194 sp-1 an-194 1A0195 sp-1 an-195 1U0195 sp-1 an-195 1C0195 sp-1 an-195 1A0196 sp-1 an-196 1U0196 sp-1 an-196 1C0196 sp-1 an-196 1A0197 sp-1 an-197 1U0197 sp-1 an-197 1C0197 sp-1 an-197 1A0198 sp-1 an-198 1U0198 sp-1 an-198 1C0198 sp-1 an-198 1A0199 sp-1 an-199 1U0199 sp-1 an-199 1C0199 sp-1 an-199 1A0200 sp-1 an-200 1U0200 sp-1 an-200 1C0200 sp-1 an-200 1A0201 sp-1 an-201 1U0201 sp-1 an-201 1C0201 sp-1 an-201 1A0202 sp-1 an-202 1U0202 sp-1 an-202 1C0202 sp-1 an-202 1A0203 sp-1 an-203 1U0203 sp-1 an-203 1C0203 sp-1 an-203 1A0204 sp-1 an-204 1U0204 sp-1 an-204 1C0204 sp-1 an-204 1A0205 sp-1 an-205 1U0205 sp-1 an-205 1C0205 sp-1 an-205 1A0206 sp-1 an-206 1U0206 sp-1 an-206 1C0206 sp-1 an-206 1A0207 sp-1 an-207 1U0207 sp-1 an-207 1C0207 sp-1 an-207 1A0208 sp-1 an-208 1U0208 sp-1 an-208 1C0208 sp-1 an-208 1A0209 sp-1 an-209 1U0209 sp-1 an-209 1C0209 sp-1 an-209 1A0210 sp-1 an-210 1U0210 sp-1 an-210 1C0210 sp-1 an-210 1A0211 sp-1 an-211 1U0211 sp-1 an-211 1C0211 sp-1 an-211 1A0212 sp-1 an-212 1U0212 sp-1 an-212 1C0212 sp-1 an-212 1A0213 sp-1 an-213 1U0213 sp-1 an-213 1C0213 sp-1 an-213 1A0214 sp-1 an-214 1U0214 sp-1 an-214 1C0214 sp-1 an-214 1A0215 sp-1 an-215 1U0215 sp-1 an-215 1C0215 sp-1 an-215 1A0216 sp-1 an-216 1U0216 sp-1 an-216 1C0216 sp-1 an-216 1A0217 sp-1 an-217 1U0217 sp-1 an-217 1C0217 sp-1 an-217 1A0218 sp-1 an-218 1U0218 sp-1 an-218 1C0218 sp-1 an-218 1A0219 sp-1 an-219 1U0219 sp-1 an-219 1C0219 sp-1 an-219 1A0220 sp-1 an-220 1U0220 sp-1 an-220 1C0220 sp-1 an-220 1A0221 sp-1 an-221 1U0221 sp-1 an-221 1C0221 sp-1 an-221 1A0222 sp-1 an-222 1U0222 sp-1 an-222 1C0222 sp-1 an-222 1A0223 sp-1 an-223 1U0223 sp-1 an-223 1C0223 sp-1 an-223 1A0224 sp-1 an-224 1U0224 sp-1 an-224 1C0224 sp-1 an-224 1A0225 sp-1 an-225 1U0225 sp-1 an-225 1C0225 sp-1 an-225 1A0226 sp-1 an-226 1U0226 sp-1 an-226 1C0226 sp-1 an-226 1A0227 sp-1 an-227 1U0227 sp-1 an-227 1C0227 sp-1 an-227 1A0228 sp-1 an-228 1U0228 sp-1 an-228 1C0228 sp-1 an-228 1A0229 sp-1 an-229 1U0229 sp-1 an-229 1C0229 sp-1 an-229 1A0230 sp-1 an-230 1U0230 sp-1 an-230 1C0230 sp-1 an-230 1A0231 sp-1 an-231 1U0231 sp-1 an-231 1C0231 sp-1 an-231 1A0232 sp-1 an-232 1U0232 sp-1 an-232 1C0232 sp-1 an-232 1A0233 sp-1 an-233 1U0233 sp-1 an-233 1C0233 sp-1 an-233 1A0234 sp-1 an-234 1U0234 sp-1 an-234 1C0234 sp-1 an-234 1A0235 sp-1 an-235 1U0235 sp-1 an-235 1C0235 sp-1 an-235 1A0236 sp-1 an-236 1U0236 sp-1 an-236 1C0236 sp-1 an-236 1A0237 sp-1 an-237 1U0237 sp-1 an-237 1C0237 sp-1 an-237 1A0238 sp-1 an-238 1U0238 sp-1 an-238 1C0238 sp-1 an-238 1A0239 sp-1 an-239 1U0239 sp-1 an-239 1C0239 sp-1 an-239 1A0240 sp-1 an-240 1U0240 sp-1 an-240 1C0240 sp-1 an-240 1A0241 sp-1 an-241 1U0241 sp-1 an-241 1C0241 sp-1 an-241 1A0242 sp-1 an-242 1U0242 sp-1 an-242 1C0242 sp-1 an-242 1A0243 sp-1 an-243 1U0243 sp-1 an-243 1C0243 sp-1 an-243 1A0244 sp-1 an-244 1U0244 sp-1 an-244 1C0244 sp-1 an-244 1A0245 sp-1 an-245 1U0245 sp-1 an-245 1C0245 sp-1 an-245 1A0246 sp-1 an-246 1U0246 sp-1 an-246 1C0246 sp-1 an-246 1A0247 sp-1 an-247 1U0247 sp-1 an-247 1C0247 sp-1 an-247 1A0248 sp-1 an-248 1U0248 sp-1 an-248 1C0248 sp-1 an-248 1A0249 sp-1 an-249 1U0249 sp-1 an-249 1C0249 sp-1 an-249 1A0250 sp-1 an-250 1U0250 sp-1 an-250 1C0250 sp-1 an-250 1A0251 sp-1 an-251 1U0251 sp-1 an-251 1C0251 sp-1 an-251 1A0252 sp-1 an-252 1U0252 sp-1 an-252 1C0252 sp-1 an-252 1A0253 sp-1 an-253 1U0253 sp-1 an-253 1C0253 sp-1 an-253 1A0254 sp-1 an-254 1U0254 sp-1 an-254 1C0254 sp-1 an-254 1A0255 sp-1 an-255 1U0255 sp-1 an-255 1C0255 sp-1 an-255 1A0256 sp-1 an-258 1U0256 sp-1 an-256 1C0256 sp-1 an-256 1A0257 sp-1 an-257 1U0257 sp-1 an-257 1C0257 sp-1 an-257 1A0258 sp-1 an-258 1U0258 sp-1 an-258 1C0258 sp-1 an-258 1A0259 sp-1 an-259 1U0259 sp-1 an-259 1C0259 sp-1 an-259 1A0260 sp-1 an-260 1U0260 sp-1 an-260 1C0260 sp-1 an-260 1A0261 sp-1 an-261 1U0261 sp-1 an-261 1C0261 sp-1 an-261 1A0262 sp-1 an-262 1U0262 sp-1 an-262 1C0262 sp-1 an-262 1A0263 sp-1 an-263 1U0263 sp-1 an-263 1C0263 sp-1 an-263 1A0264 sp-1 an-264 1U0264 sp-1 an-264 1C0264 sp-1 an-264 1A0265 sp-1 an-265 1U0265 sp-1 an-265 1C0265 sp-1 an-265 1A0266 sp-1 an-266 1U0266 sp-1 an-266 1C0266 sp-1 an-266 1A0267 sp-1 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an-248 1A4019 sp-14 an-249 1U4019 sp-13 an-249 1A4020 sp-14 an-250 1U4020 sp-13 an-250 1A4021 sp-14 an-251 1U4021 sp-13 an-251 1A4022 sp-14 an-252 1U4022 sp-13 an-252 1A4023 sp-14 an-253 1U4023 sp-13 an-253 1A4024 sp-14 an-254 1U4024 sp-13 an-254 1A4025 sp-14 an-255 1U4025 sp-13 an-255 1A4026 sp-14 an-256 1U4026 sp-13 an-256 1A4027 sp-14 an-257 1U4027 sp-13 an-257 1A4028 sp-14 an-258 1U4028 sp-13 an-258 1A4029 sp-14 an-259 1U4029 sp-13 an-259 1A4030 sp-14 an-260 1U4030 sp-13 an-260 1A4031 sp-14 an-261 1U4031 sp-13 an-261 1A4032 sp-14 an-262 1U4032 sp-13 an-262 1A4033 sp-14 an-263 1U4033 sp-13 an-263 1A4034 sp-14 an-264 1U4034 sp-13 an-264 1A4035 sp-14 an-265 1U4035 sp-13 an-265 1A4036 sp-14 an-266 1U4036 sp-13 an-266 1A4037 sp-14 an-267 1U4037 sp-13 an-267 1A4038 sp-14 an-268 1U4038 sp-13 an-268 1A4039 sp-14 an-269 1U4039 sp-13 an-269 1A4040 sp-14 an-270 1U4040 sp-13 an-270 1A4041 sp-14 an-271 1U4041 sp-13 an-271 1A4042 sp-14 an-272 1U4042 sp-13 an-272 1A4043 sp-14 an-273 1U4043 sp-13 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an-298 1A4069 sp-14 an-299 1U4069 sp-13 an-299 1A4070 sp-14 an-300 1U4070 sp-13 an-300 1A4071 sp-14 an-301 1U4071 sp-13 an-301 1A4072 sp-14 an-302 1U4072 sp-13 an-302 1A4073 sp-14 an-303 1U4073 sp-13 an-303 1A4074 sp-14 an-304 1U4074 sp-13 an-304 1A4075 sp-14 an-305 1U4075 sp-13 an-305 1A4076 sp-14 an-306 1U4076 sp-13 an-306 1A4077 sp-14 an-307 1U4077 sp-13 an-307 1A4078 sp-14 an-308 1U4078 sp-13 an-308 1A4079 sp-14 an-309 1U4079 sp-13 an-309 1A4080 sp-14 an-310 1U4080 sp-13 an-310 1A4081 sp-14 an-311 1U4081 sp-13 an-311 1A4082 sp-14 an-312 1U4082 sp-13 an-312 1A4083 sp-14 an-313 1U4083 sp-13 an-313 1A4084 sp-14 an-314 1U4084 sp-13 an-314 1A4085 sp-14 an-315 1U4085 sp-13 an-315 1A4086 sp-14 an-316 1U4086 sp-13 an-316 1A4087 sp-14 an-317 1U4087 sp-13 an-317 1A4088 sp-14 an-318 1U4088 sp-13 an-318 1A4089 sp-14 an-319 1U4089 sp-13 an-319 1A4090 sp-14 an-320 1U4090 sp-13 an-320 1A4091 sp-14 an-321 1U4091 sp-13 an-321 1A4092 sp-14 an-322 1U4092 sp-13 an-322 1A4093 sp-14 an-323 1U4093 sp-13 an-323 1A4094 sp-14 an-324 1U4094 sp-13 an-324 1A4095 sp-14 an-325 1U4095 sp-13 an-325 1A4096 sp-14 an-326 1U4096 sp-13 an-326 1A4097 sp-14 an-327 1U4097 sp-13 an-327 1A4098 sp-14 an-328 1U4098 sp-13 an-328 1A4099 sp-14 an-329 1U4099 sp-13 an-329 1A4100 sp-14 an-330 1U4100 sp-13 an-330 1A4101 sp-14 an-331 1U4101 sp-13 an-331 1A4102 sp-14 an-332 1U4102 sp-13 an-332 1A4103 sp-14 an-333 1U4103 sp-13 an-333 1A4104 sp-14 an-334 1U4104 sp-13 an-334 1A4105 sp-14 an-335 1U4105 sp-13 an-335 1A4106 sp-14 an-336 1U4106 sp-13 an-336 1A4107 sp-14 an-337 1U4107 sp-13 an-337 1A4108 sp-14 an-338 1U4108 sp-13 an-338 1A4109 sp-14 an-339 1U4109 sp-13 an-339 1A4110 sp-14 an-340 1U4110 sp-13 an-340 1A4111 sp-14 an-341 1U4111 sp-13 an-341 1A4112 sp-14 an-342 1U4112 sp-13 an-342 1A4113 sp-14 an-343 1U4113 sp-13 an-343 1A4114 sp-14 an-344 1U4114 sp-13 an-344 1A4115 sp-14 an-345 1U4115 sp-13 an-345 1A4116 sp-14 an-346 1U4116 sp-13 an-346 1A4117 sp-14 an-347 1U4117 sp-13 an-347 1A4118 sp-14 an-348 1U4118 sp-13 an-348 1A4119 sp-14 an-349 1U4119 sp-13 an-349 1A4120 sp-14 an-350 1U4120 sp-13 an-350 1A4121 sp-14 an-351 1U4121 sp-13 an-351 1A4122 sp-14 an-352 1U4122 sp-13 an-352 1A4123 sp-14 an-353 1U4123 sp-13 an-353 1A4124 sp-14 an-354 1U4124 sp-13 an-354 1A4125 sp-14 an-355 1U4125 sp-13 an-355 1A4126 sp-14 an-356 1U4126 sp-13 an-356 1A4127 sp-14 an-357 1U4127 sp-13 an-357 1A4128 sp-14 an-358 1U4128 sp-13 an-358 1A4129 sp-14 an-359 1U4129 sp-13 an-359 1A4130 sp-14 an-360 1U4130 sp-13 an-360 1A4131 sp-14 an-361 1U4131 sp-13 an-361 1A4132 sp-14 an-362 1U4132 sp-13 an-362 1A4133 sp-14 an-363 1U4133 sp-13 an-363 1A4134 sp-14 an-364 1U4134 sp-13 an-364 1A4135 sp-14 an-365 1U4135 sp-13 an-365 1A4136 sp-14 an-366 1U4136 sp-13 an-366 1A4137 sp-14 an-367 1U4137 sp-13 an-367 1A4138 sp-14 an-368 1U4138 sp-13 an-368 1A4139 sp-14 an-369 1U4139 sp-13 an-369 1A4140 sp-14 an-370 1U4140 sp-13 an-370 1A4141 sp-14 an-371 1U4141 sp-13 an-371 1A4142 sp-14 an-372 1U4142 sp-13 an-372 1A4143 sp-14 an-373 1U4143 sp-13 an-373 1A4144 sp-14 an-374 1U4144 sp-13 an-374 1A4145 sp-14 an-375 1U4145 sp-13 an-375 1A4146 sp-14 an-376 1U4146 sp-13 an-376 1A4147 sp-14 an-377 1U4147 sp-13 an-377 Y = NHCS Y = NHCSNH Y = NHCS Exempli- Exempli- Exempli- fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ 1A4148 sp-15 an-1 1U4148 sp-14 an-1 1A5279 sp-19 an-1 1A4149 sp-15 an-2 1U4149 sp-14 an-2 1A5280 sp-19 an-2 1A4150 sp-15 an-3 1U4150 sp-14 an-3 1A5281 sp-19 an-3 1A4151 sp-15 an-4 1U4151 sp-14 an-4 1A5282 sp-19 an-4 1A4152 sp-15 an-5 1U4152 sp-14 an-5 1A5283 sp-19 an-5 1A4153 sp-15 an-6 1U4153 sp-14 an-6 1A5284 sp-19 an-6 1A4154 sp-15 an-7 1U4154 sp-14 an-7 1A5285 sp-19 an-7 1A4155 sp-15 an-8 1U4155 sp-14 an-8 1A5286 sp-19 an-8 1A4156 sp-15 an-9 1U4156 sp-14 an-9 1A5287 sp-19 an-9 1A4157 sp-15 an-10 1U4157 sp-14 an-10 1A5288 sp-19 an-10 1A4158 sp-15 an-11 1U4158 sp-14 an-11 1A5289 sp-19 an-11 1A4159 sp-15 an-12 1U4159 sp-14 an-12 1A5290 sp-19 an-12 1A4160 sp-15 an-13 1U4160 sp-14 an-13 1A5291 sp-19 an-13 1A4161 sp-15 an-14 1U4161 sp-14 an-14 1A5292 sp-19 an-14 1A4162 sp-15 an-15 1U4162 sp-14 an-15 1A5293 sp-19 an-15 1A4163 sp-15 an-16 1U4163 sp-14 an-16 1A5294 sp-19 an-16 1A4164 sp-15 an-17 1U4164 sp-14 an-17 1A5295 sp-19 an-17 1A4165 sp-15 an-18 1U4165 sp-14 an-18 1A5296 sp-19 an-18 1A4166 sp-15 an-19 1U4166 sp-14 an-19 1A5297 sp-19 an-19 1A4167 sp-15 an-20 1U4167 sp-14 an-20 1A5298 sp-19 an-20 1A4168 sp-15 an-21 1U4168 sp-14 an-21 1A5299 sp-19 an-21 1A4169 sp-15 an-22 1U4169 sp-14 an-22 1A5300 sp-19 an-22 1A4170 sp-15 an-23 1U4170 sp-14 an-23 1A5301 sp-19 an-23 1A4171 sp-15 an-24 1U4171 sp-14 an-24 1A5302 sp-19 an-24 1A4172 sp-15 an-25 1U4172 sp-14 an-25 1A5303 sp-19 an-25 1A4173 sp-15 an-26 1U4173 sp-14 an-26 1A5304 sp-19 an-26 1A4174 sp-15 an-27 1U4174 sp-14 an-27 1A5305 sp-19 an-27 1A4175 sp-15 an-28 1U4175 sp-14 an-28 1A5306 sp-19 an-28 1A4176 sp-15 an-29 1U4176 sp-14 an-29 1A5307 sp-19 an-29 1A4177 sp-15 an-30 1U4177 sp-14 an-30 1A5308 sp-19 an-30 1A4178 sp-15 an-31 1U4178 sp-14 an-31 1A5309 sp-19 an-31 1A4179 sp-15 an-32 1U4179 sp-14 an-32 1A5310 sp-19 an-32 1A4180 sp-15 an-33 1U4180 sp-14 an-33 1A5311 sp-19 an-33 1A4181 sp-15 an-34 1U4181 sp-14 an-34 1A5312 sp-19 an-34 1A4182 sp-15 an-35 1U4182 sp-14 an-35 1A5313 sp-19 an-35 1A4183 sp-15 an-36 1U4183 sp-14 an-36 1A5314 sp-19 an-36 1A4184 sp-15 an-37 1U4184 sp-14 an-37 1A5315 sp-19 an-37 1A4185 sp-15 an-38 1U4185 sp-14 an-38 1A5316 sp-19 an-38 1A4186 sp-15 an-39 1U4186 sp-14 an-39 1A5317 sp-19 an-39 1A4187 sp-15 an-40 1U4187 sp-14 an-40 1A5318 sp-19 an-40 1A4188 sp-15 an-41 1U4188 sp-14 an-41 1A5319 sp-19 an-41 1A4189 sp-15 an-42 1U4189 sp-14 an-42 1A5320 sp-19 an-42 1A4190 sp-15 an-43 1U4190 sp-14 an-43 1A5321 sp-19 an-43 1A4191 sp-15 an-44 1U4191 sp-14 an-44 1A5322 sp-19 an-44 1A4192 sp-15 an-45 1U4192 sp-14 an-45 1A5323 sp-19 an-45 1A4193 sp-15 an-46 1U4193 sp-14 an-46 1A5324 sp-19 an-46 1A4194 sp-15 an-47 1U4194 sp-14 an-47 1A5325 sp-19 an-47 1A4195 sp-15 an-48 1U4195 sp-14 an-48 1A5326 sp-19 an-48 1A4196 sp-15 an-49 1U4196 sp-14 an-49 1A5327 sp-19 an-49 1A4197 sp-15 an-50 1U4197 sp-14 an-50 1A5328 sp-19 an-50 1A4198 sp-15 an-51 1U4198 sp-14 an-51 1A5329 sp-19 an-51 Y = NHCS Y = NHCSNH Y = NHCSO Exempli- Exempli- Exempli- fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ 1A4199 sp-15 an-52 1U4199 sp-14 an-52 1A5330 sp-19 an-52 1A4200 sp-15 an-53 1U4200 sp-14 an-53 1A5331 sp-19 an-53 1A4201 sp-15 an-54 1U4201 sp-14 an-54 1A5332 sp-19 an-54 1A4202 sp-15 an-55 1U4202 sp-14 an-55 1A5333 sp-19 an-55 1A4203 sp-15 an-56 1U4203 sp-14 an-56 1A5334 sp-19 an-56 1A4204 sp-15 an-57 1U4204 sp-14 an-57 1A5335 sp-19 an-57 1A4205 sp-15 an-58 1U4205 sp-14 an-58 1A5336 sp-19 an-58 1A4206 sp-15 an-59 1U4206 sp-14 an-59 1A5337 sp-19 an-59 1A4207 sp-15 an-60 1U4207 sp-14 an-60 1A5338 sp-19 an-60 1A4208 sp-15 an-61 1U4208 sp-14 an-61 1A5339 sp-19 an-61 1A4209 sp-15 an-62 1U4209 sp-14 an-62 1A5340 sp-19 an-62 1A4210 sp-15 an-63 1U4210 sp-14 an-63 1A5341 sp-19 an-63 1A4211 sp-15 an-64 1U4211 sp-14 an-64 1A5342 sp-19 an-64 1A4212 sp-15 an-65 1U4212 sp-14 an-65 1A5343 sp-19 an-65 1A4213 sp-15 an-66 1U4213 sp-14 an-66 1A5344 sp-19 an-66 1A4214 sp-15 an-67 1U4214 sp-14 an-67 1A5345 sp-19 an-67 1A4215 sp-15 an-68 1U4215 sp-14 an-68 1A5346 sp-19 an-68 1A4216 sp-15 an-69 1U4216 sp-14 an-69 1A5347 sp-19 an-69 1A4217 sp-15 an-70 1U4217 sp-14 an-70 1A5348 sp-19 an-70 1A4218 sp-15 an-71 1U4218 sp-14 an-71 1A5349 sp-19 an-71 1A4219 sp-15 an-72 1U4219 sp-14 an-72 1A5350 sp-19 an-72 1A4220 sp-15 an-73 1U4220 sp-14 an-73 1A5351 sp-19 an-73 1A4221 sp-15 an-74 1U4221 sp-14 an-74 1A5352 sp-19 an-74 1A4222 sp-15 an-75 1U4222 sp-14 an-75 1A5353 sp-19 an-75 1A4223 sp-15 an-76 1U4223 sp-14 an-76 1A5354 sp-19 an-76 1A4224 sp-15 an-77 1U4224 sp-14 an-77 1A5355 sp-19 an-77 1A4225 sp-15 an-78 1U4225 sp-14 an-78 1A5356 sp-19 an-78 1A4226 sp-15 an-79 1U4226 sp-14 an-79 1A5357 sp-19 an-79 1A4227 sp-15 an-80 1U4227 sp-14 an-80 1A5358 sp-19 an-80 1A4228 sp-15 an-81 1U4228 sp-14 an-81 1A5359 sp-19 an-81 1A4229 sp-15 an-82 1U4229 sp-14 an-82 1A5360 sp-19 an-82 1A4230 sp-15 an-83 1U4230 sp-14 an-83 1A5361 sp-19 an-83 1A4231 sp-15 an-84 1U4231 sp-14 an-84 1A5362 sp-19 an-84 1A4232 sp-15 an-85 1U4232 sp-14 an-85 1A5363 sp-19 an-85 1A4233 sp-15 an-86 1U4233 sp-14 an-86 1A5364 sp-19 an-86 1A4234 sp-15 an-87 1U4234 sp-14 an-87 1A5365 sp-19 an-87 1A4235 sp-15 an-88 1U4235 sp-14 an-88 1A5366 sp-19 an-88 1A4236 sp-15 an-89 1U4236 sp-14 an-89 1A5367 sp-19 an-89 1A4237 sp-15 an-90 1U4237 sp-14 an-90 1A5368 sp-19 an-90 1A4238 sp-15 an-91 1U4238 sp-14 an-91 1A5369 sp-19 an-91 1A4239 sp-15 an-92 1U4239 sp-14 an-92 1A5370 sp-19 an-92 1A4240 sp-15 an-93 1U4240 sp-14 an-93 1A5371 sp-19 an-93 1A4241 sp-15 an-94 1U4241 sp-14 an-94 1A5372 sp-19 an-94 1A4242 sp-15 an-95 1U4242 sp-14 an-95 1A5373 sp-19 an-95 1A4243 sp-15 an-96 1U4243 sp-14 an-96 1A5374 sp-19 an-96 1A4244 sp-15 an-97 1U4244 sp-14 an-97 1A5375 sp-19 an-97 1A4245 sp-15 an-98 1U4245 sp-14 an-98 1A5376 sp-19 an-98 1A4246 sp-15 an-99 1U4246 sp-14 an-99 1A5377 sp-19 an-99 1A4247 sp-15 an-100 1U4247 sp-14 an-100 1A5378 sp-19 an-100 1A4248 sp-15 an-101 1U4248 sp-14 an-101 1A5379 sp-19 an-101 1A4249 sp-15 an-102 1U4249 sp-14 an-102 1A5380 sp-19 an-102 1A4250 sp-15 an-103 1U4250 sp-14 an-103 1A5381 sp-19 an-103 1A4251 sp-15 an-104 1U4251 sp-14 an-104 1A5382 sp-19 an-104 1A4252 sp-15 an-105 1U4252 sp-14 an-105 1A5383 sp-19 an-105 1A4253 sp-15 an-106 1U4253 sp-14 an-106 1A5384 sp-19 an-106 1A4254 sp-15 an-107 1U4254 sp-14 an-107 1A5385 sp-19 an-107 1A4255 sp-15 an-108 1U4255 sp-14 an-108 1A5386 sp-19 an-108 1A4256 sp-15 an-109 1U4256 sp-14 an-109 1A5387 sp-19 an-109 1A4257 sp-15 an-110 1U4257 sp-14 an-110 1A5388 sp-19 an-110 1A4258 sp-15 an-111 1U4258 sp-14 an-111 1A5389 sp-19 an-111 1A4259 sp-15 an-112 1U4259 sp-14 an-112 1A5390 sp-19 an-112 1A4260 sp-15 an-113 1U4260 sp-14 an-113 1A5391 sp-19 an-113 1A4261 sp-15 an-114 1U4261 sp-14 an-114 1A5392 sp-19 an-114 1A4262 sp-15 an-115 1U4262 sp-14 an-115 1A5393 sp-19 an-115 1A4263 sp-15 an-116 1U4263 sp-14 an-116 1A5394 sp-19 an-116 1A4264 sp-15 an-117 1U4264 sp-14 an-117 1A5395 sp-19 an-117 1A4265 sp-15 an-118 1U4265 sp-14 an-118 1A5396 sp-19 an-118 1A4266 sp-15 an-119 1U4266 sp-14 an-119 1A5397 sp-19 an-119 1A4267 sp-15 an-120 1U4267 sp-14 an-120 1A5398 sp-19 an-120 1A4268 sp-15 an-121 1U4268 sp-14 an-121 1A5399 sp-19 an-121 1A4269 sp-15 an-122 1U4269 sp-14 an-122 1A5400 sp-19 an-122 1A4270 sp-15 an-123 1U4270 sp-14 an-123 1A5401 sp-19 an-123 1A4271 sp-15 an-124 1U4271 sp-14 an-124 1A5402 sp-19 an-124 1A4272 sp-15 an-125 1U4272 sp-14 an-125 1A5403 sp-19 an-125 1A4273 sp-15 an-126 1U4273 sp-14 an-126 1A5404 sp-19 an-126 1A4274 sp-15 an-127 1U4274 sp-14 an-127 1A5405 sp-19 an-127 1A4275 sp-15 an-128 1U4275 sp-14 an-128 1A5406 sp-19 an-128 1A4276 sp-15 an-129 1U4276 sp-14 an-129 1A5407 sp-19 an-129 1A4277 sp-15 an-130 1U4277 sp-14 an-130 1A5408 sp-19 an-130 1A4278 sp-15 an-131 1U4278 sp-14 an-131 1A5409 sp-19 an-131 1A4279 sp-15 an-132 1U4279 sp-14 an-132 1A5410 sp-19 an-132 1A4280 sp-15 an-133 1U4280 sp-14 an-133 1A5411 sp-19 an-133 1A4281 sp-15 an-134 1U4281 sp-14 an-134 1A5412 sp-19 an-134 1A4282 sp-15 an-135 1U4282 sp-14 an-135 1A5413 sp-19 an-135 1A4283 sp-15 an-136 1U4283 sp-14 an-136 1A5414 sp-19 an-136 1A4284 sp-15 an-137 1U4284 sp-14 an-137 1A5415 sp-19 an-137 1A4285 sp-15 an-138 1U4285 sp-14 an-138 1A5416 sp-19 an-138 1A4286 sp-15 an-139 1U4286 sp-14 an-139 1A5417 sp-19 an-139 1A4287 sp-15 an-140 1U4287 sp-14 an-140 1A5418 sp-19 an-140 1A4288 sp-15 an-141 1U4288 sp-14 an-141 1A5419 sp-19 an-141 1A4289 sp-15 an-142 1U4289 sp-14 an-142 1A5420 sp-19 an-142 1A4290 sp-15 an-143 1U4290 sp-14 an-143 1A5421 sp-19 an-143 1A4291 sp-15 an-144 1U4291 sp-14 an-144 1A5422 sp-19 an-144 1A4292 sp-15 an-145 1U4292 sp-14 an-145 1A5423 sp-19 an-145 1A4293 sp-15 an-146 1U4293 sp-14 an-146 1A5424 sp-19 an-146 1A4294 sp-15 an-147 1U4294 sp-14 an-147 1A5425 sp-19 an-147 1A4295 sp-15 an-148 1U4295 sp-14 an-148 1A5426 sp-19 an-148 1A4296 sp-15 an-149 1U4296 sp-14 an-149 1A5427 sp-19 an-149 1A4297 sp-15 an-150 1U4297 sp-14 an-150 1A5428 sp-19 an-150 1A4298 sp-15 an-151 1U4298 sp-14 an-151 1A5429 sp-19 an-151 1A4299 sp-15 an-152 1U4299 sp-14 an-152 1A5430 sp-19 an-152 1A4300 sp-15 an-153 1U4300 sp-14 an-153 1A5431 sp-19 an-153 1A4301 sp-15 an-154 1U4301 sp-14 an-154 1A5432 sp-19 an-154 1A4302 sp-15 an-155 1U4302 sp-14 an-155 1A5433 sp-19 an-155 1A4303 sp-15 an-156 1U4303 sp-14 an-156 1A5434 sp-19 an-156 1A4304 sp-15 an-157 1U4304 sp-14 an-157 1A5435 sp-19 an-157 1A4305 sp-15 an-158 1U4305 sp-14 an-158 1A5436 sp-19 an-158 1A4306 sp-15 an-159 1U4306 sp-14 an-159 1A5437 sp-19 an-159 1A4307 sp-15 an-160 1U4307 sp-14 an-160 1A5438 sp-19 an-160 1A4308 sp-15 an-161 1U4308 sp-14 an-161 1A5439 sp-19 an-161 1A4309 sp-15 an-162 1U4309 sp-14 an-162 1A5440 sp-19 an-162 1A4310 sp-15 an-163 1U4310 sp-14 an-163 1A5441 sp-19 an-163 1A4311 sp-15 an-164 1U4311 sp-14 an-164 1A5442 sp-19 an-164 1A4312 sp-15 an-165 1U4312 sp-14 an-165 1A5443 sp-19 an-165 1A4313 sp-15 an-166 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an-384 1A6545 sp-9 an-385 1U5414 sp-9 an-385 1C3906 sp-9 an-385 1A6546 sp-9 an-386 1U5415 sp-9 an-386 1C3907 sp-9 an-386 1A6547 sp-9 an-387 1U5416 sp-9 an-387 1C3908 sp-9 an-387 1A6548 sp-9 an-388 1U5417 sp-9 an-388 1C3909 sp-9 an-388 1A6549 sp-9 an-389 1U5418 sp-9 an-389 1C3910 sp-9 an-389 1A6550 sp-9 an-390 1U5419 sp-9 an-390 1C3911 sp-9 an-390 1A6551 sp-9 an-391 1U5420 sp-9 an-391 1C3912 sp-9 an-391 1A6552 sp-9 an-392 1U5421 sp-9 an-392 1C3913 sp-9 an-392 1A6553 sp-9 an-393 1U5422 sp-9 an-393 1C3914 sp-9 an-393 1A6554 sp-10 an-378 1U5423 sp-12 an-378 1C3915 sp-11 an-378 1A6555 sp-10 an-379 1U5424 sp-12 an-379 1C3916 sp-11 an-379 1A6556 sp-10 an-380 1U5425 sp-12 an-380 1C3917 sp-11 an-380 1A6557 sp-10 an-381 1U5426 sp-12 an-381 1C3918 sp-11 an-381 1A6558 sp-10 an-382 1U5427 sp-12 an-382 1C3919 sp-11 an-382 1A6559 sp-10 an-383 1U5428 sp-12 an-383 1C3920 sp-11 an-383 1A6560 sp-10 an-384 1U5429 sp-12 an-384 1C3921 sp-11 an-384 1A6561 sp-10 an-385 1U5430 sp-12 an-385 1C3922 sp-11 an-385 1A6562 sp-10 an-386 1U5431 sp-12 an-386 1C3923 sp-11 an-386 1A6563 sp-10 an-387 1U5432 sp-12 an-387 1C3924 sp-11 an-387 1A6564 sp-10 an-388 1U5433 sp-12 an-388 1C3925 sp-11 an-388 1A6565 sp-10 an-389 1U5434 sp-12 an-389 1C3926 sp-11 an-389 1A6566 sp-10 an-390 1U5435 sp-12 an-390 1C3927 sp-11 an-390 1A6567 sp-10 an-391 1U5436 sp-12 an-391 1C3928 sp-11 an-391 1A6568 sp-10 an-392 1U5437 sp-12 an-392 1C3929 sp-11 an-392 1A6569 sp-10 an-393 1U5438 sp-12 an-393 1C3930 sp-11 an-393 1A6570 sp-14 an-378 1U5439 sp-13 an-378 1A6571 sp-14 an-379 1U5440 sp-13 an-379 1A6572 sp-14 an-380 1U5441 sp-13 an-380 1A6573 sp-14 an-381 1U5442 sp-13 an-381 1A6574 sp-14 an-382 1U5443 sp-13 an-382 1A6575 sp-14 an-383 1U5444 sp-13 an-383 1A6576 sp-14 an-384 1U5445 sp-13 an-384 1A6577 sp-14 an-385 1U5446 sp-13 an-385 1A6578 sp-14 an-386 1U5447 sp-13 an-386 1A6579 sp-14 an-387 1U5448 sp-13 an-387 1A6580 sp-14 an-388 1U5449 sp-13 an-388 1A6581 sp-14 an-389 1U5450 sp-13 an-389 1A6582 sp-14 an-390 1U5451 sp-13 an-390 1A6583 sp-14 an-391 1U5452 sp-13 an-391 1A6584 sp-14 an-392 1U5453 sp-13 an-392 1A6585 sp-14 an-393 1U5454 sp-13 an-393 Y = NHCS Y = NHCSNH Y = NHCS Exempli- Exempli- Exempli- fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ 1A6586 sp-15 an-378 1U5455 sp-14 an-378 1A6634 sp-19 an-378 1A6587 sp-15 an-379 1U5456 sp-14 an-379 1A6635 sp-19 an-379 1A6588 sp-15 an-380 1U5457 sp-14 an-380 1A6636 sp-19 an-380 1A6589 sp-15 an-381 1U5458 sp-14 an-381 1A6637 sp-19 an-381 1A6590 sp-15 an-382 1U5459 sp-14 an-382 1A6638 sp-19 an-382 1A6591 sp-15 an-383 1U5460 sp-14 an-383 1A6639 sp-19 an-383 1A6592 sp-15 an-384 1U5461 sp-14 an-384 1A6640 sp-19 an-384 1A6593 sp-15 an-385 1U5462 sp-14 an-385 1A6641 sp-19 an-385 1A6594 sp-15 an-386 1U5463 sp-14 an-386 1A6642 sp-19 an-386 1A6595 sp-15 an-387 1U5464 sp-14 an-387 1A6643 sp-19 an-387 1A6596 sp-15 an-388 1U5465 sp-14 an-388 1A6644 sp-19 an-388 1A6597 sp-15 an-389 1U5466 sp-14 an-389 1A6645 sp-19 an-389 1A6598 sp-15 an-390 1U5467 sp-14 an-390 1A6646 sp-19 an-390 1A6599 sp-15 an-391 1U5468 sp-14 an-391 1A6647 sp-19 an-391 1A6600 sp-15 an-392 1U5469 sp-14 an-392 1A6648 sp-19 an-392 1A6601 sp-15 an-393 1U5470 sp-14 an-393 1A6649 sp-19 an-393 1A6602 sp-16 an-378 1U5471 sp-17 an-378 1A6650 sp-21 an-378 1A6603 sp-16 an-379 1U5472 sp-17 an-379 1A6651 sp-21 an-379 1A6604 sp-16 an-380 1U5473 sp-17 an-380 1A6652 sp-21 an-380 1A6605 sp-16 an-381 1U5474 sp-17 an-381 1A6653 sp-21 an-381 1A6606 sp-16 an-382 1U5475 sp-17 an-382 1A6654 sp-21 an-382 1A6607 sp-16 an-383 1U5476 sp-17 an-383 1A6655 sp-21 an-383 1A6608 sp-16 an-384 1U5477 sp-17 an-384 1A6656 sp-21 an-384 1A6609 sp-16 an-385 1U5478 sp-17 an-385 1A6657 sp-21 an-385 1A6610 sp-16 an-386 1U5479 sp-17 an-386 1A6658 sp-21 an-386 1A6611 sp-16 an-387 1U5480 sp-17 an-387 1A6659 sp-21 an-387 1A6612 sp-16 an-388 1U5481 sp-17 an-388 1A6660 sp-21 an-388 1A6613 sp-16 an-389 1U5482 sp-17 an-389 1A6661 sp-21 an-389 Y = NHCS Y = NHCSNH Y = NHCSO Exempli- Exempli- Exempli- fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ 1A6614 sp-16 an-390 1U5483 sp-17 an-390 1A6662 sp-21 an-390 1A6615 sp-16 an-391 1U5484 sp-17 an-391 1A6663 sp-21 an-391 1A6616 sp-16 an-392 1U5485 sp-17 an-392 1A6664 sp-21 an-392 1A6617 sp-16 an-393 1U5486 sp-17 an-393 1A6665 sp-21 an-393 1A6618 sp-18 an-378 1U5487 sp-20 an-378 1A6666 sp-22 an-378 1A6619 sp-18 an-379 1U5488 sp-20 an-379 1A6667 sp-22 an-379 1A6620 sp-18 an-380 1U5489 sp-20 an-380 1A6668 sp-22 an-380 1A6621 sp-18 an-381 1U5490 sp-20 an-381 1A6669 sp-22 an-381 1A6622 sp-18 an-382 1U5491 sp-20 an-382 1A6670 sp-22 an-382 1A6623 sp-18 an-383 1U5492 sp-20 an-383 1A6671 sp-22 an-383 1A6624 sp-18 an-384 1U5493 sp-20 an-384 1A6672 sp-22 an-384 1A6625 sp-18 an-385 1U5494 sp-20 an-385 1A6673 sp-22 an-385 1A6626 sp-18 an-386 1U5495 sp-20 an-386 1A6674 sp-22 an-386 1A6627 sp-18 an-387 1U5496 sp-20 an-387 1A6675 sp-22 an-387 1A6628 sp-18 an-388 1U5497 sp-20 an-388 1A6676 sp-22 an-388 1A6629 sp-18 an-389 1U5498 sp-20 an-389 1A6677 sp-22 an-389 1A6630 sp-18 an-390 1U5499 sp-20 an-390 1A6678 sp-22 an-390 1A6631 sp-18 an-391 1U5500 sp-20 an-391 1A6679 sp-22 an-391 1A6632 sp-18 an-392 1U5501 sp-20 an-392 1A6680 sp-22 an-392 1A6633 sp-18 an-393 1U5502 sp-20 an-393 1A6681 sp-22 an-393 Y = NHCSNH Y = NHCSNH Y = NHCNH Exempli- Exempli- Exempli- fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ 1U5503 sp-23 an-1 1U5896 sp-24 an-1 1U6289 sp-25 an-1 1U5504 sp-23 an-2 1U5897 sp-24 an-2 1U6290 sp-25 an-2 1U5505 sp-23 an-3 1U5898 sp-24 an-3 1U6291 sp-25 an-3 1U5506 sp-23 an-4 1U5899 sp-24 an-4 1U6292 sp-25 an-4 1U5507 sp-23 an-5 1U5900 sp-24 an-5 1U6293 sp-25 an-5 1U5508 sp-23 an-6 1U5901 sp-24 an-6 1U6294 sp-25 an-6 1U5509 sp-23 an-7 1U5902 sp-24 an-7 1U6295 sp-25 an-7 1U5510 sp-23 an-8 1U5903 sp-24 an-8 1U6296 sp-25 an-8 1U5511 sp-23 an-9 1U5904 sp-24 an-9 1U6297 sp-25 an-9 1U5512 sp-23 an-10 1U5905 sp-24 an-10 1U6298 sp-25 an-10 1U5513 sp-23 an-11 1U5906 sp-24 an-11 1U6299 sp-25 an-11 1U5514 sp-23 an-12 1U5907 sp-24 an-12 1U6300 sp-25 an-12 1U5515 sp-23 an-13 1U5908 sp-24 an-13 1U6301 sp-25 an-13 1U5516 sp-23 an-14 1U5909 sp-24 an-14 1U6302 sp-25 an-14 1U5517 sp-23 an-15 1U5910 sp-24 an-15 1U6303 sp-25 an-15 1U5518 sp-23 an-16 1U5911 sp-24 an-16 1U6304 sp-25 an-16 1U5519 sp-23 an-17 1U5912 sp-24 an-17 1U6305 sp-25 an-17 1U5520 sp-23 an-18 1U5913 sp-24 an-18 1U6306 sp-25 an-18 1U5521 sp-23 an-19 1U5914 sp-24 an-19 1U6307 sp-25 an-19 1U5522 sp-23 an-20 1U5915 sp-24 an-20 1U6308 sp-25 an-20 1U5523 sp-23 an-21 1U5916 sp-24 an-21 1U6309 sp-25 an-21 1U5524 sp-23 an-22 1U5917 sp-24 an-22 1U6310 sp-25 an-22 1U5525 sp-23 an-23 1U5918 sp-24 an-23 1U6311 sp-25 an-23 1U5526 sp-23 an-24 1U5919 sp-24 an-24 1U6312 sp-25 an-24 1U5527 sp-23 an-25 1U5920 sp-24 an-25 1U6313 sp-25 an-25 1U5528 sp-23 an-26 1U5921 sp-24 an-26 1U6314 sp-25 an-26 1U5529 sp-23 an-27 1U5922 sp-24 an-27 1U6315 sp-25 an-27 1U5530 sp-23 an-28 1U5923 sp-24 an-28 1U6316 sp-25 an-28 1U5531 sp-23 an-29 1U5924 sp-24 an-29 1U6317 sp-25 an-29 1U5532 sp-23 an-30 1U5925 sp-24 an-30 1U6318 sp-25 an-30 1U5533 sp-23 an-31 1U5926 sp-24 an-31 1U6319 sp-25 an-31 1U5534 sp-23 an-32 1U5927 sp-24 an-32 1U6320 sp-25 an-32 1U5535 sp-23 an-33 1U5928 sp-24 an-33 1U6321 sp-25 an-33 Y = NHCS Y = NHCSNH Y = NHCSO Exempli- Exempli- Exempli- fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ fication Z N⁺R⁵R⁶R⁷ 1U5536 sp-23 an-34 1U5929 sp-24 an-34 1U6322 sp-25 an-34 1U5537 sp-23 an-35 1U5930 sp-24 an-35 1U6323 sp-25 an-35 1U5538 sp-23 an-36 1U5931 sp-24 an-36 1U6324 sp-25 an-36 1U5539 sp-23 an-37 1U5932 sp-24 an-37 1U6325 sp-25 an-37 1U5540 sp-23 an-38 1U5933 sp-24 an-38 1U6326 sp-25 an-38 1U5541 sp-23 an-39 1U5934 sp-24 an-39 1U6327 sp-25 an-39 1U5542 sp-23 an-40 1U5935 sp-24 an-40 1U6328 sp-25 an-40 1U5543 sp-23 an-41 1U5936 sp-24 an-41 1U6329 sp-25 an-41 1U5544 sp-23 an-42 1U5937 sp-24 an-42 1U6330 sp-25 an-42 1U5545 sp-23 an-43 1U5938 sp-24 an-43 1U6331 sp-25 an-43 1U5546 sp-23 an-44 1U5939 sp-24 an-44 1U6332 sp-25 an-44 1U5547 sp-23 an-45 1U5940 sp-24 an-45 1U6333 sp-25 an-45 1U5548 sp-23 an-46 1U5941 sp-24 an-46 1U6334 sp-25 an-46 1U5549 sp-23 an-47 1U5942 sp-24 an-47 1U6335 sp-25 an-47 1U5550 sp-23 an-48 1U5943 sp-24 an-48 1U6336 sp-25 an-48 1U5551 sp-23 an-49 1U5944 sp-24 an-49 1U6337 sp-25 an-49 1U5552 sp-23 an-50 1U5945 sp-24 an-50 1U6338 sp-25 an-50 1U5553 sp-23 an-51 1U5946 sp-24 an-51 1U6339 sp-25 an-51 1U5554 sp-23 an-52 1U5947 sp-24 an-52 1U6340 sp-25 an-52 1U5555 sp-23 an-53 1U5948 sp-24 an-53 1U6341 sp-25 an-53 1U5556 sp-23 an-54 1U5949 sp-24 an-54 1U6342 sp-25 an-54 1U5557 sp-23 an-55 1U5950 sp-24 an-55 1U6343 sp-25 an-55 1U5558 sp-23 an-56 1U5951 sp-24 an-56 1U6344 sp-25 an-56 1U5559 sp-23 an-57 1U5952 sp-24 an-57 1U6345 sp-25 an-57 1U5560 sp-23 an-58 1U5953 sp-24 an-58 1U6346 sp-25 an-58 1U5561 sp-23 an-59 1U5954 sp-24 an-59 1U6347 sp-25 an-59 1U5562 sp-23 an-60 1U5955 sp-24 an-60 1U6348 sp-25 an-60 1U5563 sp-23 an-61 1U5956 sp-24 an-61 1U6349 sp-25 an-61 1U5564 sp-23 an-62 1U5957 sp-24 an-62 1U6350 sp-25 an-62 1U5565 sp-23 an-63 1U5958 sp-24 an-63 1U6351 sp-25 an-63 1U5566 sp-23 an-64 1U5959 sp-24 an-64 1U6352 sp-25 an-64 1U5567 sp-23 an-65 1U5960 sp-24 an-65 1U6353 sp-25 an-65 1U5568 sp-23 an-66 1U5961 sp-24 an-66 1U6354 sp-25 an-66 1U5569 sp-23 an-67 1U5962 sp-24 an-67 1U6355 sp-25 an-67 1U5570 sp-23 an-68 1U5963 sp-24 an-68 1U6356 sp-25 an-68 1U5571 sp-23 an-69 1U5964 sp-24 an-69 1U6357 sp-25 an-69 1U5572 sp-23 an-70 1U5965 sp-24 an-70 1U6358 sp-25 an-70 1U5573 sp-23 an-71 1U5966 sp-24 an-71 1U6359 sp-25 an-71 1U5574 sp-23 an-72 1U5967 sp-24 an-72 1U6360 sp-25 an-72 1U5575 sp-23 an-73 1U5968 sp-24 an-73 1U6361 sp-25 an-73 1U5576 sp-23 an-74 1U5969 sp-24 an-74 1U6362 sp-25 an-74 1U5577 sp-23 an-75 1U5970 sp-24 an-75 1U6363 sp-25 an-75 1U5578 sp-23 an-76 1U5971 sp-24 an-76 1U6364 sp-25 an-76 1U5579 sp-23 an-77 1U5972 sp-24 an-77 1U6365 sp-25 an-77 1U5580 sp-23 an-78 1U5973 sp-24 an-78 1U6366 sp-25 an-78 1U5581 sp-23 an-79 1U5974 sp-24 an-79 1U6367 sp-25 an-79 1U5582 sp-23 an-80 1U5975 sp-24 an-80 1U6368 sp-25 an-80 1U5583 sp-23 an-81 1U5976 sp-24 an-81 1U6369 sp-25 an-81 1U5584 sp-23 an-82 1U5977 sp-24 an-82 1U6370 sp-25 an-82 1U5585 sp-23 an-83 1U5978 sp-24 an-83 1U6371 sp-25 an-83 1U5586 sp-23 an-84 1U5979 sp-24 an-84 1U6372 sp-25 an-84 1U5587 sp-23 an-85 1U5980 sp-24 an-85 1U6373 sp-25 an-85 1U5588 sp-23 an-86 1U5981 sp-24 an-86 1U6374 sp-25 an-86 1U5589 sp-23 an-87 1U5982 sp-24 an-87 1U6375 sp-25 an-87 1U5590 sp-23 an-88 1U5983 sp-24 an-88 1U6376 sp-25 an-88 1U5591 sp-23 an-89 1U5984 sp-24 an-89 1U6377 sp-25 an-89 1U5592 sp-23 an-90 1U5985 sp-24 an-90 1U6378 sp-25 an-90 1U5593 sp-23 an-91 1U5986 sp-24 an-91 1U6379 sp-25 an-91 1U5594 sp-23 an-92 1U5987 sp-24 an-92 1U6380 sp-25 an-92 1U5595 sp-23 an-93 1U5988 sp-24 an-93 1U6381 sp-25 an-93 1U5596 sp-23 an-94 1U5989 sp-24 an-94 1U6382 sp-25 an-94 1U5597 sp-23 an-95 1U5990 sp-24 an-95 1U6383 sp-25 an-95 1U5598 sp-23 an-96 1U5991 sp-24 an-96 1U6384 sp-25 an-96 1U5599 sp-23 an-97 1U5992 sp-24 an-97 1U6385 sp-25 an-97 1U5600 sp-23 an-98 1U5993 sp-24 an-98 1U6386 sp-25 an-98 1U5601 sp-23 an-99 1U5994 sp-24 an-99 1U6387 sp-25 an-99 1U5602 sp-23 an-100 1U5995 sp-24 an-100 1U6388 sp-25 an-100 1U5603 sp-23 an-101 1U5996 sp-24 an-101 1U6389 sp-25 an-101 1U5604 sp-23 an-102 1U5997 sp-24 an-102 1U6390 sp-25 an-102 1U5605 sp-23 an-103 1U5998 sp-24 an-103 1U6391 sp-25 an-103 1U5606 sp-23 an-104 1U5999 sp-24 an-104 1U6392 sp-25 an-104 1U5607 sp-23 an-105 1U6000 sp-24 an-105 1U6393 sp-25 an-105 1U5608 sp-23 an-106 1U6001 sp-24 an-106 1U6394 sp-25 an-106 1U5609 sp-23 an-107 1U6002 sp-24 an-107 1U6395 sp-25 an-107 1U5610 sp-23 an-108 1U6003 sp-24 an-108 1U6396 sp-25 an-108 1U5611 sp-23 an-109 1U6004 sp-24 an-109 1U6397 sp-25 an-109 1U5612 sp-23 an-110 1U6005 sp-24 an-110 1U6398 sp-25 an-110 1U5613 sp-23 an-111 1U6006 sp-24 an-111 1U6399 sp-25 an-111 1U5614 sp-23 an-112 1U6007 sp-24 an-112 1U6400 sp-25 an-112 1U5615 sp-23 an-113 1U6008 sp-24 an-113 1U6401 sp-25 an-113 1U5616 sp-23 an-114 1U6009 sp-24 an-114 1U6402 sp-25 an-114 1U5617 sp-23 an-115 1U6010 sp-24 an-115 1U6403 sp-25 an-115 1U5618 sp-23 an-116 1U6011 sp-24 an-116 1U6404 sp-25 an-116 1U5619 sp-23 an-117 1U6012 sp-24 an-117 1U6405 sp-25 an-117 1U5620 sp-23 an-118 1U6013 sp-24 an-118 1U6406 sp-25 an-118 1U5621 sp-23 an-119 1U6014 sp-24 an-119 1U6407 sp-25 an-119 1U5622 sp-23 an-120 1U6015 sp-24 an-120 1U6408 sp-25 an-120 1U5623 sp-23 an-121 1U6016 sp-24 an-121 1U6409 sp-25 an-121 1U5624 sp-23 an-122 1U6017 sp-24 an-122 1U6410 sp-25 an-122 1U5625 sp-23 an-123 1U6018 sp-24 an-123 1U6411 sp-25 an-123 1U5626 sp-23 an-124 1U6019 sp-24 an-124 1U6412 sp-25 an-124 1U5627 sp-23 an-125 1U6020 sp-24 an-125 1U6413 sp-25 an-125 1U5628 sp-23 an-126 1U6021 sp-24 an-126 1U6414 sp-25 an-126 1U5629 sp-23 an-127 1U6022 sp-24 an-127 1U6415 sp-25 an-127 1U5630 sp-23 an-128 1U6023 sp-24 an-128 1U6416 sp-25 an-128 1U5631 sp-23 an-129 1U6024 sp-24 an-129 1U6417 sp-25 an-129 1U5632 sp-23 an-130 1U6025 sp-24 an-130 1U6418 sp-25 an-130 1U5633 sp-23 an-131 1U6026 sp-24 an-131 1U6419 sp-25 an-131 1U5634 sp-23 an-132 1U6027 sp-24 an-132 1U6420 sp-25 an-132 1U5635 sp-23 an-133 1U6028 sp-24 an-133 1U6421 sp-25 an-133 1U5636 sp-23 an-134 1U6029 sp-24 an-134 1U6422 sp-25 an-134 1U5637 sp-23 an-135 1U6030 sp-24 an-135 1U6423 sp-25 an-135 1U5638 sp-23 an-136 1U6031 sp-24 an-136 1U6424 sp-25 an-136 1U5639 sp-23 an-137 1U6032 sp-24 an-137 1U6425 sp-25 an-137 1U5640 sp-23 an-138 1U6033 sp-24 an-138 1U6426 sp-25 an-138 1U5641 sp-23 an-139 1U6034 sp-24 an-139 1U6427 sp-25 an-139 1U5642 sp-23 an-140 1U6035 sp-24 an-140 1U6428 sp-25 an-140 1U5643 sp-23 an-141 1U6036 sp-24 an-141 1U6429 sp-25 an-141 1U5644 sp-23 an-142 1U6037 sp-24 an-142 1U6430 sp-25 an-142 1U5645 sp-23 an-143 1U6038 sp-24 an-143 1U6431 sp-25 an-143 1U5646 sp-23 an-144 1U6039 sp-24 an-144 1U6432 sp-25 an-144 1U5647 sp-23 an-145 1U6040 sp-24 an-145 1U6433 sp-25 an-145 1U5648 sp-23 an-146 1U6041 sp-24 an-146 1U6434 sp-25 an-146 1U5649 sp-23 an-147 1U6042 sp-24 an-147 1U6435 sp-25 an-147 1U5650 sp-23 an-148 1U6043 sp-24 an-148 1U6436 sp-25 an-148 1U5651 sp-23 an-149 1U6044 sp-24 an-149 1U6437 sp-25 an-149 1U5652 sp-23 an-150 1U6045 sp-24 an-150 1U6438 sp-25 an-150 1U5653 sp-23 an-151 1U6046 sp-24 an-151 1U6439 sp-25 an-151 1U5654 sp-23 an-152 1U6047 sp-24 an-152 1U6440 sp-25 an-152 1U5655 sp-23 an-153 1U6048 sp-24 an-153 1U6441 sp-25 an-153 1U5656 sp-23 an-154 1U6049 sp-24 an-154 1U6442 sp-25 an-154 1U5657 sp-23 an-155 1U6050 sp-24 an-155 1U6443 sp-25 an-155 1U5658 sp-23 an-156 1U6051 sp-24 an-156 1U6444 sp-25 an-156 1U5659 sp-23 an-157 1U6052 sp-24 an-157 1U6445 sp-25 an-157 1U5660 sp-23 an-158 1U6053 sp-24 an-158 1U6446 sp-25 an-158 1U5661 sp-23 an-159 1U6054 sp-24 an-159 1U6447 sp-25 an-159 1U5662 sp-23 an-160 1U6055 sp-24 an-160 1U6448 sp-25 an-160 1U5663 sp-23 an-161 1U6056 sp-24 an-161 1U6449 sp-25 an-161 1U5664 sp-23 an-162 1U6057 sp-24 an-162 1U6450 sp-25 an-162 1U5665 sp-23 an-163 1U6058 sp-24 an-163 1U6451 sp-25 an-163 1U5666 sp-23 an-164 1U6059 sp-24 an-164 1U6452 sp-25 an-164 1U5667 sp-23 an-165 1U6060 sp-24 an-165 1U6453 sp-25 an-165 1U5668 sp-23 an-166 1U6061 sp-24 an-166 1U6454 sp-25 an-166 1U5669 sp-23 an-167 1U6062 sp-24 an-167 1U6455 sp-25 an-167 1U5670 sp-23 an-168 1U6063 sp-24 an-168 1U6456 sp-25 an-168 1U5671 sp-23 an-169 1U6064 sp-24 an-169 1U6457 sp-25 an-169 1U5672 sp-23 an-170 1U6065 sp-24 an-170 1U6458 sp-25 an-170 1U5673 sp-23 an-171 1U6066 sp-24 an-171 1U6459 sp-25 an-171 1U5674 sp-23 an-172 1U6067 sp-24 an-172 1U6460 sp-25 an-172 1U5675 sp-23 an-173 1U6068 sp-24 an-173 1U6461 sp-25 an-173 1U5676 sp-23 an-174 1U6069 sp-24 an-174 1U6462 sp-25 an-174 1U5677 sp-23 an-175 1U6070 sp-24 an-175 1U6463 sp-25 an-175 1U5678 sp-23 an-176 1U6071 sp-24 an-176 1U6464 sp-25 an-176 1U5679 sp-23 an-177 1U6072 sp-24 an-177 1U6465 sp-25 an-177 1U5680 sp-23 an-178 1U6073 sp-24 an-178 1U6466 sp-25 an-178 1U5681 sp-23 an-179 1U6074 sp-24 an-179 1U6467 sp-25 an-179 1U5682 sp-23 an-180 1U6075 sp-24 an-180 1U6468 sp-25 an-180 1U5683 sp-23 an-181 1U6076 sp-24 an-181 1U6469 sp-25 an-181 1U5684 sp-23 an-182 1U6077 sp-24 an-182 1U6470 sp-25 an-182 1U5685 sp-23 an-183 1U6078 sp-24 an-183 1U6471 sp-25 an-183 1U5686 sp-23 an-184 1U6079 sp-24 an-184 1U6472 sp-25 an-184 1U5687 sp-23 an-185 1U6080 sp-24 an-185 1U6473 sp-25 an-185 1U5688 sp-23 an-186 1U6081 sp-24 an-186 1U6474 sp-25 an-186 1U5689 sp-23 an-187 1U6082 sp-24 an-187 1U6475 sp-25 an-187 1U5690 sp-23 an-188 1U6083 sp-24 an-188 1U6476 sp-25 an-188 1U5691 sp-23 an-189 1U6084 sp-24 an-189 1U6477 sp-25 an-189 1U5692 sp-23 an-190 1U6085 sp-24 an-190 1U6478 sp-25 an-190 1U5693 sp-23 an-191 1U6086 sp-24 an-191 1U6479 sp-25 an-191 1U5694 sp-23 an-192 1U6087 sp-24 an-192 1U6480 sp-25 an-192 1U5695 sp-23 an-193 1U6088 sp-24 an-193 1U6481 sp-25 an-193 1U5696 sp-23 an-194 1U6089 sp-24 an-194 1U6482 sp-25 an-194 1U5697 sp-23 an-195 1U6090 sp-24 an-195 1U6483 sp-25 an-195 1U5698 sp-23 an-196 1U6091 sp-24 an-196 1U6484 sp-25 an-196 1U5699 sp-23 an-197 1U6092 sp-24 an-197 1U6485 sp-25 an-197 1U5700 sp-23 an-198 1U6093 sp-24 an-198 1U6486 sp-25 an-198 1U5701 sp-23 an-199 1U6094 sp-24 an-199 1U6487 sp-25 an-199 1U5702 sp-23 an-200 1U6095 sp-24 an-200 1U6488 sp-25 an-200 1U5703 sp-23 an-201 1U6096 sp-24 an-201 1U6489 sp-25 an-201 1U5704 sp-23 an-202 1U6097 sp-24 an-202 1U6490 sp-25 an-202 1U5705 sp-23 an-203 1U6098 sp-24 an-203 1U6491 sp-25 an-203 1U5706 sp-23 an-204 1U6099 sp-24 an-204 1U6492 sp-25 an-204 1U5707 sp-23 an-205 1U6100 sp-24 an-205 1U6493 sp-25 an-205 1U5708 sp-23 an-206 1U6101 sp-24 an-206 1U6494 sp-25 an-206 1U5709 sp-23 an-207 1U6102 sp-24 an-207 1U6495 sp-25 an-207 1U5710 sp-23 an-208 1U6103 sp-24 an-208 1U6496 sp-25 an-208 1U5711 sp-23 an-209 1U6104 sp-24 an-209 1U6497 sp-25 an-209 1U5712 sp-23 an-210 1U6105 sp-24 an-210 1U6498 sp-25 an-210 1U5713 sp-23 an-211 1U6106 sp-24 an-211 1U6499 sp-25 an-211 1U5714 sp-23 an-212 1U6107 sp-24 an-212 1U6500 sp-25 an-212 1U5715 sp-23 an-213 1U6108 sp-24 an-213 1U6501 sp-25 an-213 1U5716 sp-23 an-214 1U6109 sp-24 an-214 1U6502 sp-25 an-214 1U5717 sp-23 an-215 1U6110 sp-24 an-215 1U6503 sp-25 an-215 1U5718 sp-23 an-216 1U6111 sp-24 an-216 1U6504 sp-25 an-216 1U5719 sp-23 an-217 1U6112 sp-24 an-217 1U6505 sp-25 an-217 1U5720 sp-23 an-218 1U6113 sp-24 an-218 1U6506 sp-25 an-218 1U5721 sp-23 an-219 1U6114 sp-24 an-219 1U6507 sp-25 an-219 1U5722 sp-23 an-220 1U6115 sp-24 an-220 1U6508 sp-25 an-220 1U5723 sp-23 an-221 1U6116 sp-24 an-221 1U6509 sp-25 an-221 1U5724 sp-23 an-222 1U6117 sp-24 an-222 1U6510 sp-25 an-222 1U5725 sp-23 an-223 1U6118 sp-24 an-223 1U6511 sp-25 an-223 1U5726 sp-23 an-224 1U6119 sp-24 an-224 1U6512 sp-25 an-224 1U5727 sp-23 an-225 1U6120 sp-24 an-225 1U6513 sp-25 an-225 1U5728 sp-23 an-226 1U6121 sp-24 an-226 1U6514 sp-25 an-226 1U5729 sp-23 an-227 1U6122 sp-24 an-227 1U6515 sp-25 an-227 1U5730 sp-23 an-228 1U6123 sp-24 an-228 1U6516 sp-25 an-228 1U5731 sp-23 an-229 1U6124 sp-24 an-229 1U6517 sp-25 an-229 1U5732 sp-23 an-230 1U6125 sp-24 an-230 1U6518 sp-25 an-230 1U5733 sp-23 an-231 1U6126 sp-24 an-231 1U6519 sp-25 an-231 1U5734 sp-23 an-232 1U6127 sp-24 an-232 1U6520 sp-25 an-232 1U5735 sp-23 an-233 1U6128 sp-24 an-233 1U6521 sp-25 an-233 1U5736 sp-23 an-234 1U6129 sp-24 an-234 1U6522 sp-25 an-234 1U5737 sp-23 an-235 1U6130 sp-24 an-235 1U6523 sp-25 an-235 1U5738 sp-23 an-236 1U6131 sp-24 an-236 1U6524 sp-25 an-236 1U5739 sp-23 an-237 1U6132 sp-24 an-237 1U6525 sp-25 an-237 1U5740 sp-23 an-238 1U6133 sp-24 an-238 1U6526 sp-25 an-238 1U5741 sp-23 an-239 1U6134 sp-24 an-239 1U6527 sp-25 an-239 1U5742 sp-23 an-240 1U6135 sp-24 an-240 1U6528 sp-25 an-240 1U5743 sp-23 an-241 1U6136 sp-24 an-241 1U6529 sp-25 an-241 1U5744 sp-23 an-242 1U6137 sp-24 an-242 1U6530 sp-25 an-242 1U5745 sp-23 an-243 1U6138 sp-24 an-243 1U6531 sp-25 an-243 1U5746 sp-23 an-244 1U6139 sp-24 an-244 1U6532 sp-25 an-244 1U5747 sp-23 an-245 1U6140 sp-24 an-245 1U6533 sp-25 an-245 1U5748 sp-23 an-246 1U6141 sp-24 an-246 1U6534 sp-25 an-246 1U5749 sp-23 an-247 1U6142 sp-24 an-247 1U6535 sp-25 an-247 1U5750 sp-23 an-248 1U6143 sp-24 an-248 1U6536 sp-25 an-248 1U5751 sp-23 an-249 1U6144 sp-24 an-249 1U6537 sp-25 an-249 1U5752 sp-23 an-250 1U6145 sp-24 an-250 1U6538 sp-25 an-250 1U5753 sp-23 an-251 1U6146 sp-24 an-251 1U6539 sp-25 an-251 1U5754 sp-23 an-252 1U6147 sp-24 an-252 1U6540 sp-25 an-252 1U5755 sp-23 an-253 1U6148 sp-24 an-253 1U6541 sp-25 an-253 1U5756 sp-23 an-254 1U6149 sp-24 an-254 1U6542 sp-25 an-254 1U5757 sp-23 an-255 1U6150 sp-24 an-255 1U6543 sp-25 an-255 1U5758 sp-23 an-256 1U6151 sp-24 an-256 1U6544 sp-25 an-256 1U5759 sp-23 an-257 1U6152 sp-24 an-257 1U6545 sp-25 an-257 1U5760 sp-23 an-258 1U6153 sp-24 an-258 1U6546 sp-25 an-258 1U5761 sp-23 an-259 1U6154 sp-24 an-259 1U6547 sp-25 an-259 1U5762 sp-23 an-260 1U6155 sp-24 an-260 1U6548 sp-25 an-260 1U5763 sp-23 an-261 1U6156 sp-24 an-261 1U6549 sp-25 an-261 1U5764 sp-23 an-262 1U6157 sp-24 an-262 1U6550 sp-25 an-262 1U5765 sp-23 an-263 1U6158 sp-24 an-263 1U6551 sp-25 an-263 1U5766 sp-23 an-264 1U6159 sp-24 an-264 1U6552 sp-25 an-264 1U5767 sp-23 an-265 1U6160 sp-24 an-265 1U6553 sp-25 an-265 1U5768 sp-23 an-266 1U6161 sp-24 an-266 1U6554 sp-25 an-266 1U5769 sp-23 an-267 1U6162 sp-24 an-267 1U6555 sp-25 an-267 1U5770 sp-23 an-268 1U6163 sp-24 an-268 1U6556 sp-25 an-268 1U5771 sp-23 an-269 1U6164 sp-24 an-269 1U6557 sp-25 an-269 1U5772 sp-23 an-270 1U6165 sp-24 an-270 1U6558 sp-25 an-270 1U5773 sp-23 an-271 1U6166 sp-24 an-271 1U6559 sp-25 an-271 1U5774 sp-23 an-272 1U6167 sp-24 an-272 1U6560 sp-25 an-272 1U5775 sp-23 an-273 1U6168 sp-24 an-273 1U6561 sp-25 an-273 1U5776 sp-23 an-274 1U6169 sp-24 an-274 1U6562 sp-25 an-274 1U5777 sp-23 an-275 1U6170 sp-24 an-275 1U6563 sp-25 an-275 1U5778 sp-23 an-276 1U6171 sp-24 an-276 1U6564 sp-25 an-276 1U5779 sp-23 an-277 1U6172 sp-24 an-277 1U6565 sp-25 an-277 1U5780 sp-23 an-278 1U6173 sp-24 an-278 1U6566 sp-25 an-278 1U5781 sp-23 an-279 1U6174 sp-24 an-279 1U6567 sp-25 an-279 1U5782 sp-23 an-280 1U6175 sp-24 an-280 1U6568 sp-25 an-280 1U5783 sp-23 an-281 1U6176 sp-24 an-281 1U6569 sp-25 an-281 1U5784 sp-23 an-282 1U6177 sp-24 an-282 1U6570 sp-25 an-282 1U5785 sp-23 an-283 1U6178 sp-24 an-283 1U6571 sp-25 an-283 1U5786 sp-23 an-284 1U6179 sp-24 an-284 1U6572 sp-25 an-284 1U5787 sp-23 an-285 1U6180 sp-24 an-285 1U6573 sp-25 an-285 1U5788 sp-23 an-286 1U6181 sp-24 an-286 1U6574 sp-25 an-286 1U5789 sp-23 an-287 1U6182 sp-24 an-287 1U6575 sp-25 an-287 1U5790 sp-23 an-288 1U6183 sp-24 an-288 1U6576 sp-25 an-288 1U5791 sp-23 an-289 1U6184 sp-24 an-289 1U6577 sp-25 an-289 1U5792 sp-23 an-290 1U6185 sp-24 an-290 1U6578 sp-25 an-290 1U5793 sp-23 an-291 1U6186 sp-24 an-291 1U6579 sp-25 an-291 1U5794 sp-23 an-292 1U6187 sp-24 an-292 1U6580 sp-25 an-292 1U5795 sp-23 an-293 1U6188 sp-24 an-293 1U6581 sp-25 an-293 1U5796 sp-23 an-294 1U6189 sp-24 an-294 1U6582 sp-25 an-294 1U5797 sp-23 an-295 1U6190 sp-24 an-295 1U6583 sp-25 an-295 1U5798 sp-23 an-296 1U6191 sp-24 an-296 1U6584 sp-25 an-296 1U5799 sp-23 an-297 1U6192 sp-24 an-297 1U6585 sp-25 an-297 1U5800 sp-23 an-298 1U6193 sp-24 an-298 1U6586 sp-25 an-298 1U5801 sp-23 an-299 1U6194 sp-24 an-299 1U6587 sp-25 an-299 1U5802 sp-23 an-300 1U6195 sp-24 an-300 1U6588 sp-25 an-300 1U5803 sp-23 an-301 1U6196 sp-24 an-301 1U6589 sp-25 an-301 1U5804 sp-23 an-302 1U6197 sp-24 an-302 1U6590 sp-25 an-302 1U5805 sp-23 an-303 1U6198 sp-24 an-303 1U6591 sp-25 an-303 1U5806 sp-23 an-304 1U6199 sp-24 an-304 1U6592 sp-25 an-304 1U5807 sp-23 an-305 1U6200 sp-24 an-305 1U6593 sp-25 an-305 1U5808 sp-23 an-306 1U6201 sp-24 an-306 1U6594 sp-25 an-306 1U5809 sp-23 an-307 1U6202 sp-24 an-307 1U6595 sp-25 an-307 1U5810 sp-23 an-308 1U6203 sp-24 an-308 1U6596 sp-25 an-308 1U5811 sp-23 an-309 1U6204 sp-24 an-309 1U6597 sp-25 an-309 1U5812 sp-23 an-310 1U6205 sp-24 an-310 1U6598 sp-25 an-310 1U5813 sp-23 an-311 1U6206 sp-24 an-311 1U6599 sp-25 an-311 1U5814 sp-23 an-312 1U6207 sp-24 an-312 1U6600 sp-25 an-312 1U5815 sp-23 an-313 1U6208 sp-24 an-313 1U6601 sp-25 an-313 1U5816 sp-23 an-314 1U6209 sp-24 an-314 1U6602 sp-25 an-314 1U5817 sp-23 an-315 1U6210 sp-24 an-315 1U6603 sp-25 an-315 1U5818 sp-23 an-316 1U6211 sp-24 an-316 1U6604 sp-25 an-316 1U5819 sp-23 an-317 1U6212 sp-24 an-317 1U6605 sp-25 an-317 1U5820 sp-23 an-318 1U6213 sp-24 an-318 1U6606 sp-25 an-318 1U5821 sp-23 an-319 1U6214 sp-24 an-319 1U6607 sp-25 an-319 1U5822 sp-23 an-320 1U6215 sp-24 an-320 1U6608 sp-25 an-320 1U5823 sp-23 an-321 1U6216 sp-24 an-321 1U6609 sp-25 an-321 1U5824 sp-23 an-322 1U6217 sp-24 an-322 1U6610 sp-25 an-322 1U5825 sp-23 an-323 1U6218 sp-24 an-323 1U6611 sp-25 an-323 1U5826 sp-23 an-324 1U6219 sp-24 an-324 1U6612 sp-25 an-324 1U5827 sp-23 an-325 1U6220 sp-24 an-325 1U6613 sp-25 an-325 1U5828 sp-23 an-326 1U6221 sp-24 an-326 1U6614 sp-25 an-326 1U5829 sp-23 an-327 1U6222 sp-24 an-327 1U6615 sp-25 an-327 1U5830 sp-23 an-328 1U6223 sp-24 an-328 1U6616 sp-25 an-328 1U5831 sp-23 an-329 1U6224 sp-24 an-329 1U6617 sp-25 an-329 1U5832 sp-23 an-330 1U6225 sp-24 an-330 1U6618 sp-25 an-330 1U5833 sp-23 an-331 1U6226 sp-24 an-331 1U6619 sp-25 an-331 1U5834 sp-23 an-332 1U6227 sp-24 an-332 1U6620 sp-25 an-332 1U5835 sp-23 an-333 1U6228 sp-24 an-333 1U6621 sp-25 an-333 1U5836 sp-23 an-334 1U6229 sp-24 an-334 1U6622 sp-25 an-334 1U5837 sp-23 an-335 1U6230 sp-24 an-335 1U6623 sp-25 an-335 1U5838 sp-23 an-336 1U6231 sp-24 an-336 1U6624 sp-25 an-336 1U5839 sp-23 an-337 1U6232 sp-24 an-337 1U6625 sp-25 an-337 1U5840 sp-23 an-338 1U6233 sp-24 an-338 1U6626 sp-25 an-338 1U5841 sp-23 an-339 1U6234 sp-24 an-339 1U6627 sp-25 an-339 1U5842 sp-23 an-340 1U6235 sp-24 an-340 1U6628 sp-25 an-340 1U5843 sp-23 an-341 1U6236 sp-24 an-341 1U6629 sp-25 an-341 1U5844 sp-23 an-342 1U6237 sp-24 an-342 1U6630 sp-25 an-342 1U5845 sp-23 an-343 1U6238 sp-24 an-343 1U6631 sp-25 an-343 1U5846 sp-23 an-344 1U6239 sp-24 an-344 1U6632 sp-25 an-344 1U5847 sp-23 an-345 1U6240 sp-24 an-345 1U6633 sp-25 an-345 1U5848 sp-23 an-346 1U6241 sp-24 an-346 1U6634 sp-25 an-346 1U5849 sp-23 an-347 1U6242 sp-24 an-347 1U6635 sp-25 an-347 1U5850 sp-23 an-348 1U6243 sp-24 an-348 1U6636 sp-25 an-348 1U5851 sp-23 an-349 1U6244 sp-24 an-349 1U6637 sp-25 an-349 1U5852 sp-23 an-350 1U6245 sp-24 an-350 1U6638 sp-25 an-350 1U5853 sp-23 an-351 1U6246 sp-24 an-351 1U6639 sp-25 an-351 1U5854 sp-23 an-352 1U6247 sp-24 an-352 1U6640 sp-25 an-352 1U5855 sp-23 an-353 1U6248 sp-24 an-353 1U6641 sp-25 an-353 1U5856 sp-23 an-354 1U6249 sp-24 an-354 1U6642 sp-25 an-354 1U5857 sp-23 an-355 1U6250 sp-24 an-355 1U6643 sp-25 an-355 1U5858 sp-23 an-356 1U6251 sp-24 an-356 1U6644 sp-25 an-356 1U5859 sp-23 an-357 1U6252 sp-24 an-357 1U6645 sp-25 an-357 1U5860 sp-23 an-358 1U6253 sp-24 an-358 1U6646 sp-25 an-358 1U5861 sp-23 an-359 1U6254 sp-24 an-359 1U6647 sp-25 an-359 1U5862 sp-23 an-360 1U6255 sp-24 an-360 1U6648 sp-25 an-360 1U5863 sp-23 an-361 1U6256 sp-24 an-361 1U6649 sp-25 an-361 1U5864 sp-23 an-362 1U6257 sp-24 an-362 1U6650 sp-25 an-362 1U5865 sp-23 an-363 1U6258 sp-24 an-363 1U6651 sp-25 an-363 1U5866 sp-23 an-364 1U6259 sp-24 an-364 1U6652 sp-25 an-364 1U5867 sp-23 an-365 1U6260 sp-24 an-365 1U6653 sp-25 an-365 1U5868 sp-23 an-366 1U6261 sp-24 an-366 1U6654 sp-25 an-366 1U5869 sp-23 an-367 1U6262 sp-24 an-367 1U6655 sp-25 an-367 1U5870 sp-23 an-368 1U6263 sp-24 an-368 1U6656 sp-25 an-368 1U5871 sp-23 an-369 1U6264 sp-24 an-369 1U6657 sp-25 an-369 1U5872 sp-23 an-370 1U6265 sp-24 an-370 1U6658 sp-25 an-370 1U5873 sp-23 an-371 1U6266 sp-24 an-371 1U6659 sp-25 an-371 1U5874 sp-23 an-372 1U6267 sp-24 an-372 1U6660 sp-25 an-372 1U5875 sp-23 an-373 1U6268 sp-24 an-373 1U6661 sp-25 an-373 1U5876 sp-23 an-374 1U6269 sp-24 an-374 1U6662 sp-25 an-374 1U5877 sp-23 an-375 1U6270 sp-24 an-375 1U6663 sp-25 an-375 1U5878 sp-23 an-376 1U6271 sp-24 an-376 1U6664 sp-25 an-376 1U5879 sp-23 an-377 1U6272 sp-24 an-377 1U6665 sp-25 an-377 1U5880 sp-23 an-378 1U6273 sp-24 an-378 1U6666 sp-25 an-378 1U5881 sp-23 an-379 1U6274 sp-24 an-379 1U6667 sp-25 an-379 1U5882 sp-23 an-380 1U6275 sp-24 an-380 1U6668 sp-25 an-380 1U5883 sp-23 an-381 1U6276 sp-24 an-381 1U6669 sp-25 an-381 1U5884 sp-23 an-382 1U6277 sp-24 an-382 1U6670 sp-25 an-382 1U5885 sp-23 an-383 1U6278 sp-24 an-383 1U6671 sp-25 an-383 1U5886 sp-23 an-384 1U6279 sp-24 an-384 1U6672 sp-25 an-384 1U5887 sp-23 an-385 1U6280 sp-24 an-385 1U6673 sp-25 an-385 1U5888 sp-23 an-386 1U6281 sp-24 an-386 1U6674 sp-25 an-386 1U5889 sp-23 an-387 1U6282 sp-24 an-387 1U6675 sp-25 an-387 1U5890 sp-23 an-388 1U6283 sp-24 an-388 1U6676 sp-25 an-388 1U5891 sp-23 an-389 1U6284 sp-24 an-389 1U6677 sp-25 an-389 1U5892 sp-23 an-390 1U6285 sp-24 an-390 1U6678 sp-25 an-390 1U5893 sp-23 an-391 1U6286 sp-24 an-391 1U6679 sp-25 an-391 1U5894 sp-23 an-392 1U6287 sp-24 an-392 1U6680 sp-25 an-392 1U5895 sp-23 an-393 1U6288 sp-24 an-393 1U6681 sp-25 an-393

Moreover, mention may be made of compounds (from 2A0001 to 2A6681, from 2U0001 to 2U6681, and from 2C0001 to 2C3930) which are identical to the compounds described in Table 1 (from 1A0001 to 1A6681, from 1U0001 to 1U6681, and from 1C0001 to 1C3930) except that the bonding position of Y has been changed to the para-position. Here, it means that, for example, compound 1A0001 has been changed to compound 2A0001. The same is true for the following.

Moreover, mention may be made of compounds (from 3A0001 to 3A6681, from 3U0001 to 3U6681, and from 3C0001 to 3C3930) which are identical to the compounds described in Table 1 (from 1A0001 to 1A6681, from 1U0001 to 1U6681, and from 1C0001 to 1C3930) except that the NR³R⁴ has been replaced by a 7-diethylamino group.

Moreover, mention may be made of compounds (from 4A0001 to 4A6681, from 4U0001 to 4U6681, and from 4C0001 to 4C3930) which are identical to the compounds described in Table 1 (from 1A0001 to 1A6681, from 1U0001 to 1U6681, and from 1C0001 to 1C3930) except that the NR3R4 has been replaced by a 7-ethylmethylamino group.

Moreover, mention may be made of compounds (from 5A0001 to 5A6681, from 5U0001 to 5U6681, and from 5C0001 to 5C3930) which are identical to the compounds described in Table 1 (from 1A0001 to 1A6681, from 1U0001 to 1U6681, and from 1C0001 to 1C3930) except that the NR³R⁴ has been replaced by a 9-dimethylamino group.

Moreover, mention may be made of compounds (from 6A0001 to 6A6681, from 6U0001 to 6U6681, and from 6C0001 to 6C3930) which are identical to the compounds described in Table 1 (from 1A0001 to 1A6681, from 1U0001 to 1U6681, and from 1C0001 to 1C3930) except that the NR³R⁴ has been replaced by a 7,9-bis (dimethylamino) group.

Moreover, mention may be made of compounds (from 7A0001 to 7A6681, from 7U0001 to 7U6681, and from 7C0001 to 7C3930) which are identical to the compounds described in Table 1 (from 1A0001 to 1A6681, from 1U0001 to 1U6681, and from 1C0001 to 1C3930) except that both R1 and R2 have been replaced by propyl groups, respectively.

Moreover, mention may be made of compounds (from 8A0001 to 8A6681, from 8U0001 to 8U6681, and from 8C0001 to 8C3930) which are identical to the compounds described in Table 1 (from 1A0001 to 1A6681, from 1U0001 to 1U6681, and from 1C0001 to 1C3930) except that both R¹ and R² have been replaced by pentyl groups, respectively.

Moreover, mention may be made of compounds (from 9A0001 to 9A6681, from 9U0001 to 9U6681, and from 9C0001 to 9C3930) which are identical to the compounds described in Table 1 (from 1A0001 to 1A6681, from 1U0001 to 1U6681, and from 1C0001 to 1C3930) except that both R¹ and R² have been replaced by hexyl groups, respectively.

Moreover, mention may be made of compounds (from 10A0001 to 10A6681, from 10U0001 to 10U6681, and from 1000001 to 10C3930) which are identical to the compounds (from 1A0001 to 1A6681, from 1U0001 to 1U6681, and from 100001 to 1C3930) except that the R¹ thereof has been replaced by an ethyl group.

The compounds represented by the formula (1) of the present invention can be produced by the following production method.

(Production Method)

Among the compounds represented by the formula (1), those compounds in which Y is —NHCS— can be obtained by allowing a compound represented by the following formula (2)

[wherein R5, R6, and R7 are as mentioned earlier, and the quaternary ammonium structure mentioned earlier has been changed to a tertiary amine structure] to react on a compound represented by the following formula (3)

[wherein R1, R2, R3, R4, m, n, and Z are as mentioned earlier; Y represents an —NHCS—; and X represents a group which can become an anion].

The reaction is carried out, for example, at room temperature or 40 to 100° C optionally in a solvent such as acetonitrile or N,N-dimethylformamide (hereinafter, “DMF” for short) by allowing at least an equimolar amount, preferably 1 to 5 time molar amount of the compound represented by the formula (2) to react on the compound represented by the formula (3) for 1 to 48 hours.

X in the formula (3) is a group which undergoes nucleophilic substitution by the compound represented by the formula (2) and is released as an anion, preferably a group which is released as a pharmaceutically acceptable anion. Preferable examples thereof include F, Cl, Br, I, mesylate, and tosylate, and more preferably Cl, Br, and I.

Compounds represented by the formula (2) include compounds represented by formulae from (ta-1) to (ta-407). Letters next to the formula numbers indicate names of manufacturing companies as follows. “AC” stands for ACROSS ORGANICS, “AL” stands for ALDRICH CHEMICAL COMPANY “BO” stands for BIO-NET CHEMICAL CO. LTD., “FL” stands for FLUKA CHEMICAL CORPORATION “IC” stands for ICN-RF, “LN” stands for LANCASTER CHEMICAL CO. LTD., “MY” stands for MAYBRIDGE CHEMICALS, “NC” stands for NACALAI CO. LTD., “PF” stands for PFALZ & BAUER, “SG” stands for SIGMA CHEMICAL COMPANY “SL” stands for SALOR CHEMICAL COMPANY, “TK” stands for TOKYO CHEMICAL INDUSTRIES, LTD., “WK” stands for WAKO PURE CHEMICAL INDUSTRIES LTD., and “WT” stands for WATANABE CHEMICAL INDUSTRIES LTD. ta-37 is prepared by allowing benzyl bromide manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with dipropylamine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-56 is prepared by allowing 3-bromopropanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with dibutylamine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-57 is prepared by allowing 4-bromobutanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with dibutylamine in the presence of potassium carbonate. ta-117 is prepared by neutralizing its hydrochloride manufactured by SALOR CHEMICAL COMPANY. ta-137 is prepared by allowing benzyl bromide to react with N-ethyl ethanolamine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-138 is prepared by allowing benzyl bromide to react with N-propylethanolamine manufactured by ALDRICH CHEMICAL COMPANY in the presence of potassium carbonate. ta-139 is prepared by allowing benzyl bromide to react with N-butylethanolamine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-145 is prepared by neutralizing a hydrochloride manufactured by ALDRICH CHEMICAL COMPANY. ta-148 is prepared by neutralizing its hydrochloride manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. ta-152 is prepared by allowing benzyl bromide to react with ta-99. ta-153 is prepared by allowing benzyl bromide to react with ta-100. ta-154 is prepared by allowing benzyl bromide to react with ta-101. ta-155 is prepared by allowing benzyl bromide to react with ta-105. ta-156 is prepared by allowing benzyl bromide to react with ta-106. ta-157 is prepared by allowing benzyl bromide to react with ta-108. ta-158 is prepared by allowing benzyl bromide to react with ta-112. ta-162 is prepared by allowing pentyl iodide manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with pyrrolidine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-172 is prepared by neutralizing its hydrochloride manufactured by MAYBRIDGE CHEMICALS. ta-178 is prepared by neutralizing its hydrochloride manufactured by NACALAI CO. LTD. ta-181 is prepared by allowing butyl iodide manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with piperidine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-182 is prepared by allowing pentyl iodide to react with piperidine in the presence of potassium carbonate. ta-185 is prepared by allowing benzyl bromide to react with piperidine in the presence of potassium carbonate. ta-193 is prepared by allowing sodium borohydride to react with ta-207. ta-212 is prepared by neutralizing its hydrochloride manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.. ta-234 is prepared by allowing pentyl iodide to react with morpholine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta.-237 is prepared by allowing benzyl bromide to react with morpholine in the presence of potassium carbonate. ta-255 is prepared by allowing ethyl iodide manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with piperazine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-256 is prepared by allowing butyl iodide to react with piperazine in the presence of potassium carbonate. ta-257 is manufactured by allowing pentyl iodide to react with piperazine in the presence of potassium carbonate. ta-259 is prepared by allowing benzyl bromide to react with piperazine in the presence of potassium carbonate. ta-264 is prepared by allowing benzyl bromide to react with ta-254. ta-265 is prepared by allowing benzyl bromide to react with ta-256. ta-266 is prepared by allowing benzyl bromide to react with ta-260. ta-279 is prepared by allowing butyl iodide to react with azepane manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-280 is prepared by allowing pentyl iodide to react with azepane in the presence of potassium carbonate. ta-281 is prepared by allowing benzyl bromide to react with azepane in the presence of potassium carbonate. ta-290 is prepared by neutralizing its hydrochloride manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.. ta-294 is prepared by allowing phenylacetyl chloride manufactured by ALDRICH CHEMICAL COMPANY to react with 3-aminoquinuclidine hydrochloride manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-295 is prepared by allowing butyl chloride manufactured by ALDRICH CHEMICAL COMPANY to react with 3-aminoquinuclidine hydrochloride in the presence of potassium carbonate. ta-296 is prepared by allowing valeryl chloride manufactured by ALDRICH CHEMICAL COMPANY to react with 3-aminoquinuclidine hydrochloride in the presence of potassium carbonate. ta-298 is prepared by allowing butyl bromide manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with ta-297. ta-299 is prepared by allowing benzyl bromide to react with ta-297. (ta-1) to (ta-407) correspond to (an-1) to (an-407) mentioned earlier, respectively.

The compounds represented by the formula (3) can be obtained by allowing compounds of the formula (4-1) below

[wherein R¹, R², R³, R⁴, m, n, Z, and X are as mentioned earlier; Y′ represents an —NHCO—, provided that the —NH in the —NHCO— represents a bond which links with an adjacent benzene ring and CO— represents a bond which links with an adjacent Z] to react with various sulfurizing agents.

The reaction is carried out, for example, at room temperature or 50 to 100° C in a solvent such as tetrahydrofuran (hereinafter, “THF” for short), 1,4-dioxane, or toluene, by allowing the compound represented by the formula (4-1) to react with at least an equimolar amount, preferably 1 to 10 time molar amount of a sulfurizing agent for 1 to 48 hours. Examples of preferable sulfurizing agent include Lawesson's reagent (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) and diphosphorus pentasulfide (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.).

The substituting position of Y in the formula (4-1) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position, and most preferably a meta-position. The compound represented by the formula (4-1) can be obtained by allowing a compound represented by formula (5-1) below

[where n, Z, and X are as mentioned earlier; and L¹ represents a leaving group] to react with a compound represented by the following formula (6-1)

[where R¹, R², R³, R⁴, and m are as mentioned earlier].

The reaction is carried out, for example, by allowing at least an equimolar amount, preferably 1 to 1.2 time molar amount of the compound represented by the formula (5-1) to react with the compound represented by the formula (6-1), in a solvent such as dichloromethane or THF in the presence of an excess amount, preferably 1 .5 to 3 time molar amount of a base, preferably an organic base such as triethylamine or an inorganic base such as potassium carbonate, at room temperature to 60° C for 1 to 24 hours.

L¹ in the formula (5-1) is a group which undergoes nucleophilic substitution by the compound represented by the formula (6-1) and is released. Preferable examples of such a group include F, Cl, Br, I, mesylate and tosylate, with Cl and Br being more preferable. L¹ and X may be mutually different, but it is also preferable that L¹ and X are equal to each other. Examples of preferable compounds represented by the formula (5-1) include 3-bromopropionyl chloride (ac-1), 4-bromobutyryl chloride (ac-2), 5-bromovaleryl chloride (ac-3), 6-bromo-n-caproyl chloride (ac-4) (all the ac-1 to ac-4 are manufacture by TOKYO CHEMICAL INDUSTRIES, LTD.), 7-bromo-n-heptanoyl chloride (ac-5), (prepared by oxidizing 7-bromo-1-heptanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. with chromium (VI) oxide in the presence of concentrated sulfuric acid and then allowing thionyl chloride to react with the resultant), 8-bromo-n-octanoyl chloride (ac-6) (prepared by allowing thionyl chloride to react with 8-bromooctanoic acid manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 9-bromo-n-nonanoyl chloride (ac-7) (prepared by oxidizing 9-bromo-1-nonanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. with chromium oxide (VI) in the presence of concentrated sulfuric acid and then allowing thionyl chloride to react with the resultant), 10-bromo-n-decanoyl chloride (ac-8) (prepared by allowing thionyl chloride to react with 10-bromodecanoic acid manufactured by PFALZ & BAUER), 11-bromo-n-undecanoyl chloride (ac-9) (prepared by allowing thionyl chloride to react with 11-bromoundecanoic acid manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 3-bromo-2-methylpropionyl chloride (ac-10) (prepared by allowing thionyl chloride to react with 3-bromo-2-methylpropionic acid manufactured by FLUKA CHEMICAL CORPORATION), 4-(chloromethyl)benzoyl chloride (ac-1l) (manufactured by ALDRICH CHEMICAL COMPANY), 4-(bromomethyl)phenylacetyl chloride (ac-12) (prepared by allowing thionyl chloride to react with 4-(bromomethyl) phenylacetic acid manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 2-[4-(bromomethyl)phenyl] propionyl chloride (ac-13) (prepared by allowing thionyl chloride to react with 2-[4-(bromomethyl)phenyl] propionic acid manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 3-(bromomethyl)phenoxyacetyl chloride (ac-14) (prepared by allowing thionyl chloride to react with 3-(bromomethyl)phenoxyacetic acid manufactured by LANCASTER), 3-bromo-2-(bromomethyl)propionyl chloride (ac-15) (prepared by allowing thionyl chloride to react with 3-bromo-2-(bromomethyl)propionic acid manufactured by ALDRICH CHEMICAL COMPANY), 3-bromoacryloyl chloride (ac-16) (prepared by allowing thionyl chloride to react with 3-bromoacrylic acid manufactured by MAYBRIDGE CHEMICALS), and 3-(bromomethyl)crotonyl chloride (ac-17) (prepared by allowing thionyl chloride to react with 3-(bromomethyl)crotonic acid manufactured by SALOR CHEMICAL COMPANY).

The substituting position of a primary amino group in the formula (6-1) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position, and more preferably a meta-position.

Among the compounds represented by the formula (1), those compounds in which Y represents —NHCS— can be obtained by allowing various sulfurizing agents to react with compounds represented by the following formula (4-2)

[wherein R¹, R², R³, R⁴, m, n, R⁵, R⁶, R⁷, Y′, Z, and X⁻ are as mentioned earlier].

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 10 time molar amount of the sulfurizing agent to react with the compound represented by the formula (4-2) in a solvent such as ethanol, 1,4-dioxane, chloroform, or 1,2-dichioroethane, at room temperature or at 50° C to 100° C, for 1 to 48 hours. Examples of preferable sulfurizing agent include Lawesson's reagent and diphosphorus pentasulfide.

The compounds represented by the formula (4-2) are obtained by allowing the compound represented by the formula (2) to react with the compound represented by the formula (4-1).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 5 time molar amount of the compound represented by the formula (2) to react with the compound represented by the formula (4-1) optionally in a solvent such as acetonitrile or DMF at room temperature or40 to 100° C for 1 to 48 hours.

Among the compounds represented by the formula (1), those compounds in which Y represents —NHCSNH— can be obtained by allowing a compound represented by formula (5-2a)

[wherein n, R⁵, R⁶, R⁷, Z, and X⁻ are as mentioned earlier] to react with the compound represented by the formula (6-1).

The reaction is carried out, for example, by allowing an equimolar amount of the compound represented by the formula (5-2a) to react with the compound represented by the formula (6-1) in a solvent such as chloroform, acetonitrile, or DMF at room temperature or at 40° C to 100° C for 1 to 48 hours.

The compound represented by the formula (5-2a) can be obtained by allowing the compound represented by the formula (2) to react with a compound represented by formula (5-2b) below

[wherein n, Z, and X are as mentioned earlier].

The reaction is carried out, for example, by allowing at least equimolar amount, preferably 1 to 5 time molar amount of the compound represented by the formula (2) to react with the compound represented by the formula (5-2b) optionally in a solvent such as acetonitrile or DMF at room temperature or at 40° C to 100° C for 1 to 48 hours.

Examples of the compound represented by the formula (5-2b) include 2-bromoethyl isothiocyanate (is-1), 3-bromopropyl isothiocyanate (is-2), (both is-1and is-2 are manufactured by TRANS WORLD CHEMICAL CORPORATION), 4-bromobutyl isothiocyanate (is-3) (prepared by brominating 4-aminobutanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. with hydrobromic acid and then allowing thiophosgene to react with the resultant according to the method described in Canadian Journal of Chemistry, Vol. 49, 971-974, 1971), 5-bromopentyl isothiocyanate (is-4) (prepared similarly from 5-aminopentanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 6-bromohexyl isothiocyanate (is-5) (prepared similarly from 6-aminohexanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 7-bromoheptyl isothiocyanate (is-6) (prepared similarly from 7-aminoheptanol manufactured by WATANABE CHEMICAL INDUSTRIES LTD.), 8-bromooctyl isothiocyanate (is-7) (prepared similarly from 8-aminooctanol manufactured by WATANABE CHEMICAL INDUSTRIES LTD.), 9-bromononyl isothiocyanate (is-8) (prepared similarly from 9-aminononanol manufactured by WATANABE CHEMICAL INDUSTRIES LTD.), 10-bromodecyl isothiocyanate (is-9) (prepared similarly from 10-aminodecanol manufactured by WATANABE CHEMICAL INDUSTRIES LTD.), 3-bromo-2,2-dimethylpropyl isothiocyanate (is-10) (prepared similarly from 3-amino-2,2-dimethylpropanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 5-bromo-4,4-dimethylpentyl isothiocyanate (is-11) (prepared similarly from 5-amino-2,2-dimethylpentanol manufactured by ICN-RF, 2-(2-bromoethoxy)ethyl isothiocyanate (is-12) (prepared similarly from 2-(2-aminoethoxy)ethanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 2,2-bis(bromomethyl)butyl isothiocyanate (is-13) (prepared similarly from 2-(aminoethyl)-2-ethyl-1,3-propanediol manufactured by SALOR CHEMICAL COMPANY), 4-(bromomethyl)phenyl isothiocyanate (is-14) (prepared from p-tolyl isothiocyanate manufactured by ALDRICH CHEMICAL COMPANY according to the method described in Journal of Heterocyclic Chemistry, Vol. 31, 457-480, 1994), 3-(bromomethyl)phenyl isothiocyanate (is-15) (prepared from m-tolyl isothiocyanate manufactured by ALDRICH CHEMICAL COMPANY according to the method described in the same document as above), 2-(bromomethyl)phenyl isothiocyanate (is-16) (prepared from 0-tolyl isothiocyanate manufactured by ALDRICH CHEMICAL COMPANY according to the method described in the same document as above), 4-(2-bromoethyl)phenyl isothiocyanate (is-17) (prepared by brominating 2-(4-aminophenyl)ethanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. with hydrobromic acid and then allowing thiophosgene to react with the resultant according to the method described in Canadian Journal of Chemistry, Vol. 49, 971-974, 1971). Among the compounds represented by the formula (1), those compounds in which Y is —NHCSO— are obtained by allowing a compound represented by formula (5-3a) below

[wherein n, R⁵, R⁶, R⁷, Z, and X⁻ are as mentioned earlier] to react with a compound represented by formula (6-2) below

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier].

The reaction is carried out, for example, by allowing an equimolar amount of the compound represented by the formula (5-3a) to react with the compound represented by the formula (6-2) in a solvent such as THF, 1,4-dioxane, or 2-ethoxyethyl ether in the presence of an equimolar amount or more, preferably 1 to 5 time molar amount of a base, preferably an inorganic base such as sodium hydride or metallic sodium at 50° C to 150° C, for 1 to 48 hours.

The substituting position of the —NCS in the formula (6-2) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position, and most preferably a meta-position.

The compound represented by the formula (5-3a) are obtained by allowing the compound represented by the formula (2) to react on a compound represented by formula (5-3b) HO—Z—(X)n  (5-3 b) [wherein n, Z, and X are as mentioned earlier].

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 5 time molar amount of the compound represented by the formula (2) to react with the compound represented by the formula (5-3b), optionally in a solvent such as acetonitrile or DMF, at room temperature or at 40° C to 100° C for 1 to 48 hours.

Examples of compounds represented by the formula (5-3b) include 2-bromoethanol (al-1), 3-bromopropanol (al-2), 4-bromobutanol (al-3), 5-bromopentanol (al-4), 6-bromohexanol (al-5), 7-bromoheptanol (al-6), 8-bromooctanol (al-7), 9-bromononanol (al-8), 10-bromodecanol (al-9) (all the compounds al-1to al-9 are manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 3-bromo-2-methylpropanol (al-10), and 3-bromo-2,2-dimethylpropanol (al-1l) (the compounds al-10 and al-11 are manufactured by ALDRICH CHEMICAL COMPANY).

The compound represented by the formula (6-2) is obtained by allowing thiophosgene to react with the compound represented by the formula (6-1).

The reaction is carried out, for example, by allowing an equimolar amount of thiophosgene (manufactured by ALDRICH CHEMICAL COMPANY) to react with the compound represented by the formula (6-1), optionally in a solvent such as THF or dichloromethane, in the presence of an equimolar amount or more, preferably 1 to 5 time molar amount of a base, preferably an organic base such as triethylamine, at room temperature or 0 to 100C for 1 to 24 hours.

The compound represented by the formula (6-1) is obtained by subjecting a compound represented by formula (7-2a) below

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier] to hydrogenation, reaction with hydroxylamine, or acid hydrolysis according to the method described in literature (Tetrahedron Letters, Vol. 38, 6367-6370, 1997).

In the case of the hydrogenation, the reaction is carried out, for example, by addition of hydrogen gas to the compound represented by the formula (7-2a) in a solvent such as methanol, ethyl acetate, or 1,4-dioxane in the presence of 1 mole % to 30 mole % of a catalytic reduction catalyst, at room temperature or at 40° C to 100 ° for 1 to 24 hours. Examples of a preferable catalytic reduction catalyst include palladium and platinum.

In the case of the reaction with hydroxylamine, the reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 3 time molar amount of hydroxylamine hydrochloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) to react with the compound represented by the formula (7-2a) in a solvent such as methanol in the presence of an equimolar or more, preferably 1 to 5 time molar amount of a base such as sodium acetate at room temperature for 1 to 24 hours.

In the case of acid hydrolysis, the reaction is carried out, for example, by allowing an excess amount, preferably 30 to 300 time molar amount of an acid, preferably 1 N to 5 N hydrochloric acid to react with the compound represented by the formula (7-2a), optionally in a solvent such as THF or methanol, at room temperature for 1 to 24 hours.

The substituting position of the imino group in the formula (7-2a) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position.

The compound represented by the formula (7-2a) is obtained by allowing benzophenonimine to react with a compound represented by formula (7-2b) below

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier] according to the method described in literature (Tetrahedron Letters, Vol. 38, 6367-6370, 1997).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 5 time molar amount of benzophenonimine (manufactured by ALDRICH CHEMICAL COMPANY) to react with the compound represented by the formula (7-2b) in a solvent such as THF, 1,4-dioxane, or toluene in the presence of an organic palladium compound such as 0.1 mole % to 10 mole % of palladium (II) acetate or an organic phosphorus compound such as 0.1 mole % to 10 mole % of 2,2′-bis(diphenylphosphenyl)-1,1-binaphthyl, and an inorganic base such as 1 to 3 time molar amount of cesium carbonate at room temperature or at 40 ° to 100 ° for 1 to 24 hours.

The substituting position of trifluoromesylate in the formula (7-2b) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and para-position. Trifluoromesylate in the formula (7-2b) may be replaced by a mesylate or a tosylate.

The compound represented by the formula (7-2b) is obtained by allowing trifluoromethanesulfonic acid anhydride to react with a compound represented by formula (7-2c) below

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier].

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 3 time molar amount of trifluoromethanesulfonic acid anhydride (manufactured by ALDRICH CHEMICAL COMPANY) to react with the compound represented by the formula (6-1), optionally in a solvent such as THF or dichioromethane, in the presence of an equimolar or more, preferably 1 to 20 time molar amount of a base, preferably an organic base such as triethylamine, at room temperature or at 0° C to 10° C for 1 to 24 hours. Compounds in which the trifluoromesylate in the formula (7-2b) is replaced by a mesylate or a tosylate, are obtained by allowing mesyl chloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) or tosyl chloride (manufactured by ALDRICH CHEMICAL COMPANY), respectively, instead of the trifluoromethanesulfonic acid anhydride to react with the compound represented by the formula (6-1).

The substituting position of the hydroxyl group in the formula (7-2c) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position. The compound represented by the formula (7-2c) is obtained by allowing Lewis acid, pyridine hydrochloride, or trimethylsilane iodide to react with a compound represented by the following formula (7-2d) below

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier].

The reaction is carried out, for example, by allowing an equimolar amount or more of any one of various Lewis acids, such as aluminum chloride, boron trihalide, titanium tetrachloride, and tin tetrachloride, pyridine hydrochloride, or trimethylsilane iodide to react with the compound represented by the formula (7-2d) in a solvent such as dichloromethane at 0° C to 10° C, room temperature, or 50° C to 150° C, for 1 to 24 hours. Preferably, the reaction is carried out, for example, by allowing a 2 to 5 time molar amount of boron trihalide, preferably boron tribromide, in a solvent such as dichloromethane at room temperature or 0° C to 10° C for 1 to 5 hours.

The substituting position of the methoxy group in the formula (7-2d) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position.

The compound represented by the formula (7-2d) is obtained by reducing a compound which is selected from compounds represented by formula (8) below

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier; and W represents a methoxy group or a nitro group] and in which W is a methoxy group.

The reaction is carried out, for example, by allowing an equimolar amount or more of any one of various reducing agents such as sodium borohydride, sodium cyanohydride, borane, and lithium aluminum hydride, preferably sodium borohydride or borane to react with the compound represented by the formula (8) in which W is a methoxy group in a solvent such as methanol or THF at room temperature or while heating for 1 hour or more. In particular, it is preferable to allow a 20 to 50 time molar amount of borane to react in THF at room temperature for 1 to 5 hours.

When W in the formuia (8) is a methoxy group, the substituting position may be any one of an ortho-position, a meta-position, and a para-position, preferably a para-position. When W is a nitro group, the substituting position is a meta-position.

Among the compounds represented by the formula (6-1), a compound of which the substituting position of the primary amino group is the meta-position is also obtained by reducing a compound represented by the following formula (7-1) below

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier].

The reaction is carried out, for example, by allowing an equimolar amount or more of any one of various reducing agents such as sodium borohydride, sodium cyanohydride, borane, or lithium aluminum hydride, preferably sodium borohydride or borane to react with the compound represented by the formula (7-1) in a solvent such as methanol or THF at room temperature or while heating for 1 hour or more. In particular, it is preferable to allow a 20 to 50 time molar amount of borane to react in THF at room temperature for 1 to 5 hours.

The compound represented by the formula (7-1) is obtained by reducing a compound represented by the formula (8) in which W is a nitro group at the meta-position.

The reaction is carried out, for example, by addition of hydrogen gas to the compound represented by the formula (8) in which W is a nitro group at the meta-position in a solvent such as methanol, ethyl acetate or 1 ,4-dioxane in the presence of 1 mole % to 30 mole % of a catalytic reduction catalyst at room temperature or at 40° C to 100° C for 1 to 24 hours. Examples of preferable catalytic reduction catalyst include palladium and platinum.

The compound represented by the formula (8) is obtained by allowing a compound represented by formula (9) below

[wherein R³ and R⁴ are as mentioned earlier] to react with a compound represented by formula (10-1) below

[where R¹, R², m, and W are as mentioned earlier; and L³ represents a halogen].

The reaction is carried out, for example, by allowing an excess amount, preferably a 10 to 50 time molar amount of the compound represented by the formula (9) to react with the compound represented by the formula (10-1), optionally in a solvent such as THF, dioxane, or methanol, at 50° C to 150° C, for 5 to 72 hours.

Examples of the halogen represented by L³ in the formula (10-1) include F, Cl, Br, and I, preferably F and Cl, with F being most preferable. L³ may substitute at any one of the 6- to 9-positions. It is preferable that either the 7-position or the 9-position is mono-substituted or the 7- and 9-positions are di-substituted with L³. It is more preferable that the 7-position is mono-substituted with L³.

Examples of the compounds represented by the formula (9) include dimethylamine, diethylamine, and ethylmethylamine (all the three compounds are manufactured by ALDRICH CHEMICAL COMPANY).

Among the compounds represented by formula (10-1), a compound in which W is a methoxy group is obtained by oxidizing a compound represented by formula (11) below

[wherein R¹, R², R³, m, and W′ are as mentioned earlier; and W′ represents a methoxy group or a hydrogen atom] in which W′ is a methoxy group.

The reaction is carried out, for example, by allowing an equimolar amount or more of any one of various oxidizing agents such as hydrogen peroxide, metachloroperbenzoic acid, and oxone, or an equimolar amount or more of sodium periodate in the presence of a catalytic amount of ruthenium trichloride to react with the compound represented by the formula (11) in which W⁻ is a methoxy group in a solvent such as trifluoroacetic acid, dichloromethane, methanol, acetonitrile or water under ice cooling or at room temperature for 1 hour or more. In particular, it is preferable to allow a 2 to 5 time molar amount of sodium periodate to react in a dichloromethane-acetonitrile-water mixed solvent in the presence of a 0.05 to 0.2 time molar amount of ruthenium trichloride at room temperature for 5 to 48 hours.

When W′ in the formula (11) is a methoxy group, the substituting position thereof may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position or a para-position.

Among the compounds represented by the formula (10-1), a compound in which W is a nitro group is obtained by nitration of a compound represented by formula (10-2) below

[where R¹, R², R³, and m are as explained earlier].

The reaction is carried out, for example, by allowing an excess molar amount of nitric acid and sulfuric acid, preferably a 10 to 40 time molar amount of fuming nitric acid and a 10 to 20 time molar amount of concentrated sulfuric acid, to react with the compound represented by the formula (10-2) at 0° C to 10° C or at room temperature for 30 minutes to 3 hours.

The compound represented by the formula (10-2) is obtained by oxidizing the compound represented by the formula (11) in which W′ is a hydrogen atom.

The reaction is carried out, for example, by allowing an equimolar amount or more of various oxidizing agents such as hydrogen peroxide, metachloroperbenzoic acid, or oxone, or an equimolar amount or more of sodium periodate in the presence of a catalytic amount of ruthenium trichioride to react with the compound of the formula (11) in which W′ is a hydrogen atom, in a solvent such as trifluoroacetic acid, dichloromethane, methanol, acetonitrile, or water, under ice cooling or at room temperature for 1 hour or more. In particular, it is preferable to allow a 2 to 5 time molar amount of sodium periodate to react in a dichloromethane-acetonitrile-water mixed solvent, in the presence of a 0.05 to 0.2 time molar amount of ruthenium trichloride at room temperature for 5 to 48 hours.

The compound represented by the formula (11) is obtained by dehydrating a compound represented by formula (12) below

[wherein R¹, R², L³, m, and W′ are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, in a solvent such as 2,6-lutidine, toluene, or xylene in the presence of a 0.1 to 1 time molar amount of an acid such as hydrochloric acid, toluenesulfonic acid, or camphorsulfonic acid, preferably toluenesulfonic acid, at 100° C to 150° C for 10 to 36 hours.

The compound represented by the formula (12) is obtained by allowing a compound represented by formula (13) below

[where R¹ and R² are as mentioned earlier] to react with a compound represented by formula (14) below

[where L³, m, and W′ are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an equimolar amount of the compound represented by the formula (13) to react with the compound represented by the formula (14) in a solvent such as a butyl acetate-water mixed solvent in the presence of an excess amount, preferably 3 to 5 time molar amount of inorganic base such as sodium hydroxide at 60° C to 120° C for 1 to 5 hours.

The compound represented by the formula (14) is obtained by allowing a base to react with a compound represented by formula (15-1) below

[wherein L³, m, and W′ are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an excess amount, preferably a 3 to 10 time molar amount of an inorganic base such as potassium hydroxide to react with the compound represented by the formula (15-1), in a solvent such as methanol, THF, or dioxane, at 50° C to 100° C for 1 to 24 hours.

Among the compounds represented by the formula (14), a compound in which W′ is a hydrogen atom is also obtained by allowing a metal sulfide compound to react with a compound represented by formula (15-2) below

[wherein L³ and m are as mentioned earlier; and L⁴ represents a halogen].

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 1 .5 time molar amount of a metal sulfide compound such as lithium sulfide or sodium sulfide to react with the compound represented by the formula (15-2) in a solvent such as dimethyl sulfoxide (hereinafter, “DMSO” for short) or DMF at 100° C to 150° C for 1 to 5 hours.

Examples of halogen represented by L⁴ in the formula (15-2) include F, Cl, Br, and I, preferably F and Cl, with F being most preferable. L³ and L⁴ may be different; however, it is preferable that L³ and L⁴ are the same.

The compound represented by the formula (15-1) is obtained by heat treatment of a compound represented by formula (16) below

(wherein L³, m, and W′ are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by heat treatment optionally in a solvent such as tetradecane or diphenyl ether, at 200° C to 300° C for 1 to 24 hours.

The compound represented by the formula (16) is obtained by allowing N,N-dimethylthiocarbamoyl chloride to react with a compound represented by formula (17) below

[wherein L³, m, and W′ are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably a 1 to 1.5 time molar amount of N,N-dimethylthiocarbamoyl chloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) to react with the compound represented by the formula (16) in a solvent such as THF or dioxane in the presence of an excess amount, preferably a 1.5 to 3 time molar amount of an organic base such as triethylamine, and a catalytic amount, preferably a 0.1 to 0.2 time molar amount of a strong organic base such as dimethylaminopyridine or an equimolar amount or more, preferably a 1 to 1.5 time molar amount of an inorganic base such as sodium hydride at room temperature or at 50° C to 100° C for 1 to 24 hours.

The compound represented by the formula (17) is obtained by allowing a compound represented by formula (18) below

[where W′ is as mentioned earlier] to react with a compound represented by formula (19) below

[wherein L³ and m are as mentioned earlier] according to the method described in literature (see Chemistry Letters, 823-824, 1996). The reaction is carried out, for example, by allowing a 2 time molar amount of the compound represented by the formula (18) to react with the compound represented by the formula (19) in a solvent such as DMF in the presence of a 0.05 time molar amount of palladium chloride, a 0.2 time molar amount of lithium chloride, and a 2 time molar amount of sodium carbonate at 100° C to 150° C for 1 to 24 hours.

Examples of the compounds represented by the formula (18) include 4-iodoanisole, 3-iodoanisole, and iodobenzene (all the three are manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.).

Examples of the compound represented by the formula (19) include 5-fluorosalicyl aldehyde (manufactured by APOLLO CHEMICAL COMPANY LTD.), and 3-fluorosalicyl aldehyde (manufactured by ALDRICH CHEMICAL COMPANY).

Furthermore, the compound represented by the formula (17) is also obtained by allowing a Lewis acid to react with a compound represented by formula (20) below

[where L³, m, and W′ are as mentioned earlier] according to the method described in literature (Journal of Compounds and Radiopharmaceuticals, Vol. 34, 643-652, 1994).

The reaction is carried out, for example, by allowing an excess amount, preferably a 1.5 to 5 time molar amount of a Lewis acid, preferably titanium tetrachloride or aluminum chloride, more preferably titanium tetrachloride to react with the compound represented by the formula (20), optionally in a solvent such as nitrobenzene at 120° C to 160° C, for 1 to 24 hours.

The compound represented by the formula (20) is obtained by allowing a compound represented by formula (21) below

[where L³ and m are as mentioned earlier] to react with a compound represented by formula (22) below

[where W′ is as mentioned earlier] according to the method described in literature (see Journal of Compounds and Radiopharmaceuticals, Vol. 34, 643-652, 1994).

The reaction is carried out, for example, by allowing an equimolar amount of the compound represented by the formula (22) to react with the compound represented by the formula (21), in a solvent such as dichloromethane, chloroform or THF, in the presence of an equimolar amount, preferably a 1 to 1.5 time molar amount of an organic base such as triethylamine at 40° C to 60° C for 1 to 5 hours.

Examples of the compounds represented by the formula (21) include 4-fluorophenol, 2-fluorophenol, and 2,4-difluorophenol (all the three are manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.).

Examples of the compounds represented by the formula (22) include 4-methoxybenzoyl chloride, 3-methoxybenzoyl chloride, and benzoyl chloride (all the three are manufactured by ALDRICH CHEMICAL COMPANY).

The compound represented by the formula (13) is obtained by allowing chlorosulfonic acid to react with a compound represented by formula (23) below

[wherein R¹ and R² are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 2 time molar amount of chiorosulfonic acid to react with the compound represented by the formula (23) in a solvent such as dichloromethane at 0° to 10° C or at room temperature for 1 to 24 hours.

The compound represented by the formula (23) is obtained by reducing a compound represented by formula (24) below

[where R¹ and R² are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an excess molar amount, preferably a 1.5 to 3 time molar amount of lithium aluminum hydride to react with the compound represented by the formula (23) in a solvent such as THE at room temperature or at 50° C to 60° C for 1 to 5 hours.

The compound represented by the formula (24) is obtained by hydrolyzing, with an acid, of a compound represented by formula (25) below

[where R¹ and R² are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an excess amount, preferably a 30 to 300 time molar amount of an acid, preferably 1 N to 5 N hydrochloric acid to react with the compound represented by the formula (25), optionally in a solvent such as THF or methanol, at room temperature for 1 to 24 hours.

The compound represented by the formula (25) is obtained by allowing a base to react with a compound represented by formula (26) below

[where R¹ is as mentioned earlier] and then allowing a compound represented by formula (27) below R²—L⁵  (27) [where R² is as mentioned earlier; and L⁵ represents a halogen] to react with the resultant according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 1.5 time molar amount of an inorganic base such as sodium hydride to react with the compound represented by the formula (26) in a solvent such as DMF at room temperature or at 0° C to 10° C for 1 to 3 hours and then allowing an equimolar amount or more, preferably 1 to 1.5 time molar amount of the compound represented by the formula (27) to react with the resultant at 0° C to 10° C or at room temperature for 1 to 24 hours.

Examples of the halogen represented by L⁵ in the formula (27) include F, Cl, Br, and I, preferably Br and I, with I being more preferable.

Examples of the compounds represented by the formula (27) include iodoethane, 1-iodopropane, 1-iodobutane, 1-iodopentane, and 1-iodohexane (all are manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.).

The compound represented by the formula (26) is obtained by allowing benzaldehyde to react with a compound represented by formula (28) below

[where R¹ is as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 1.2 time molar amount of benzaldehyde (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.) to react with the compound represented by the formula (28) in the presence of an excess amount, preferably 2 to 3 time molar amount of an organic base such as triethylamine and an excess amount, preferably a 1.5 to 2 time molar amount of a dehydrating agent such as anhydrous magnesium sulfate in a solvent such as dichloromethane at room temperature for 1 to 24 hours.

Examples of the compound represented by the formula (28) include methyl 2-aminobutyrate hydrochloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), methyl 2-aminohexanoate hydrochloride (manufactured by BACH EM CHEMICAL COMPANY), methyl 2-aminopentanoate hydrochloride (prepared by allowing thionyl chloride to react with norvaline manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in methanol according to the method described in WO93/16055), methyl 2-aminoheptanoate hydrochloride, (prepared similarly from 2-aminoheptanoic acid manufactured by FLUKA CHEMICAL CORPORATION), and methyl 2-aminooctanoate hydrochloride (prepared similarly from 2-aminocaprylic acid manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.).

The compounds represented by the formula (1) can have a plurality of stereoisomers depending on the number of asymmetric centers. Those isomers which are in a relationship of diastereomers can be separated by silica gel column chromatography or fractionating crystallization during the synthesis of any one of the compounds represented by the formulae (1), (3), (4-1), (4-2), (6-1), (6-2), and from (7-2a) to (7-2d). Moreover, those isomers which are in a relationship of enantiomers can be separated by column chromatography which uses an optically active carrier or separated by silica gel column chromatography or fractionating crystallization after they are derived to diastereomers, during the synthesis of any one of the compounds represented by the formulae (1), (3), (4-1), (4-2), (6-1), (6-2), and from (7-2a) to (7-2d). On the other hand, geometric isomers can be separated by silica gel column chromatography or fractionating crystallization during the synthesis of any one of the compounds represented by the formulae (1), (3), (4-1), and (4-2).

The compounds represented by the formula (1) of the present invention include the acid addition salts. The acid addition salts are preferably pharmaceutically acceptable salts that include, for example, various types of known salts, such as hydrochlorides, hydrobromides, sulfates, hydrogen sulfates, dihydrogen phosphates, citrates, maleates, tartarates, fumarates, gluconates, and methanesulfonates. When acid addition salts are to be made, addition of an equimolar amount or a few time molar amount of an acid component to the compounds represented by the formula (1) can provide acid addition salts thereof. Examples of the acid component which can be used include pharmaceutically acceptable mineral acids or organic acids, such as hydrochloric acid, hydrobromic acid, sulfuric acid, hydrogen sulfuric acid, dihydrogen phosphoric acid, citric acid, maleic acid, tartaric acid, fumaric acid gluconic acid, and methanesulfonic acid.

The compounds of the present invention have ileal bile acid transporter inhibiting activities and have blood cholesterol-lowering effects, and ameliorating effects for cholestasis-caused hepatopathy. Therefore, it has been verified that the compounds of the present invention can be used as cholesterol-lowering agents and as ameliorating agents for cholestasis-caused hepatopathy. No case of death has been observed when the compounds of the present invention were orally administered to rats in a dosage of 3 mg per kg of body weight twice a day for 3.5 days. Furthermore, the compounds of the present invention showed no microbe mutagenicity, which indicates that the compounds of the present invention can be used safely.

Specific examples of the cholesterol-lowering agent include pharmaceutical compositions for the treatment and prevention of any one of hyperlipidemia, arteriosclerosis, and syndrome X. Detailed explanation of these disorders is as follows.

That is, examples of hyperlipidemia include hyperchylomicronemia, low density lipoprotein (LDL) hyperlipoproteinemia, familial hypercholesterolemia, very low density lipoprotein (VLDL) hyperlipoproteinemia, hypertriglyceridemia, and disorders resulting from combinations of these. Atherioscierosis may be mentioned as a preferable example of target arteriosclerosis which is subjected to treatment and prevention in the present invention. Syndrome X, as explained earlier, is a disorder which sometimes is one of the causes of hyperlipidemia and sometimes causes arteriosclerosis eventually.

The compounds of the present invention and pharmaceutical compositions containing the same are also useful as drugs for the treatment and prevention of cholestasis-caused hepatopathy and are particularly useful as drugs for the treatment and prevention of primary biliary cirrhosis and primary sclerosing cholangitis. Cholestasis means a state where eventually bile is not excreted from liver to duodenum for some reason. Once cholestasis occurs, it causes liver disorder, which is called as cholestasis-caused hepatopathy. Specific examples of hepatopathy caused by cholestasis include primary biliary cirrhosis, primary sclerosing cholangitis, and cholestatic hepatitis (cholangiolitic hepatitis) (Medical Encyclopedia published by Nanzando, 1333-1 334). Direct causes of cholestasis may include gallstones, etc. developed in bile duct or gall bladder. Primary biliary cirrhosis and primary sclerosing cholangitis are disorders which are not caused directly by gallstones.

The compounds of the present invention and pharmaceutical compositions containing the same are also useful as drugs for the treatment and prevention of obesity and fatty liver. Obesity means a state where fat is excessively accumulated in the body and specifically means a Body Mass Index (BMI) of more than 26 (Yoshio Ikeda et al., Nippon Rinsho (Japan Clinical), 53:229-236, 1995). Fatty liver means a state where usually, neutral fat is accumulated in large quantities in liver; in general, liver in which fat droplets are accumulated in approximately 30% or more of hepatic lobules is defined as fatty liver (Kyoichiro Tojima et al., Nippon Rinsho (Japan Clinical), 53:354-358, 1995).

Moreover, the compounds of the present invention and pharmaceutical compositions containing the same are also useful as drugs for the treatment and prevention of steatohepatitis. Steatohepatitis means a disease in which deposition of fat in the liver and inflammation and fibrillation of hepatic parenchyma are observed and steatohepatitis is a quite different disease from fatty liver in that steatohepatitis is accompanied by an image of inflammation (see Toshifumi Azuma et al., .KAN·TAN·SUI, 44:429-433, 2002). Among the steatohepatitis cases, those which show no causal relation to alcohol uptake are termed nonalcoholic steatohepatitis (NASH).

Upon manufacturing drugs of the present invention, it is preferable to make a pharmaceutical composition by optionally adding a pharmaceutically acceptable carrier to an effective amount of the compound represented by the formula (1) or its salts. Examples of the pharmaceutically acceptable carriers include an excipient, a binder such as carboxymethyl cellulose, a disintegrating agent, a lubricant, and an additive. The compounds of the present invention can be administered orally to humans in the form of a tablet, a powder, a granule, a capsule, a sugar coated tablet, a liquid, a syrup and so forth. Dosages may vary according to the age, weight, and symptom of a patient. Generally, in the case of an adult, a dosage of 0.1 mg to 500 mg is administered once a day or in a plural of times a day in portions. Administration period is as follows. Generally, the drug is administered everyday for a few weeks to a few months. However, the dosage and the administration period of the drug may be increased or decreased according to the symptom of the patient.

Moreover, the inventors of the present invention have studied on the pharmacological activity of various known ileal bile acid transporter (IBAT) inhibiting compounds. As a result, it has been verified that these IBAT inhibiting compounds have treating and preventing effects for cholestasis-caused hepatopathy and that these compounds can be used as drugs for the treatment and prevention of cholestasis-caused hepatopathy, particularly for the treatment and prevention of primary biliary cirrhosis and primary sclerosing cholangitis.

Thus, the present invention relates to a pharmaceutical composition which contains an IBAT inhibiting compound as an active ingredient and is effective for the treatment or prevention of cholestasis-ca used hepatopathy. Preferable examples of the pharmaceutical composition which is effective for the treatment or prevention of cholestasis-caused hepatopathy include pharmaceutical compositions for the treatment or prevention of primary biliary cirrhosis or primary sclerosing cholangitis.

As mentioned earlier, cholestasis means a state where eventually bile is not excreted from liver to duodenum for some reason. Once cholestasis occurs, it sometimes causes liver disorder, which is called as cholestasis-caused hepatopathy. Specific examples of cholestasis-caused hepatopathy include primary biliary cirrhosis, primary sclerosing cholangitis, and cholestatic hepatitis (cholangiolitic hepatitis) (see Medical Encyclopedia published by Nanzando, 1333-1334). Furthermore, direct causes of cholestasis may include gallstones developed in bile duct or gall bladder. Primary biliary cirrhosis and primary sclerosing cholangitis are disorders which are not caused directly by gallstones. Primary biliary cirrhosis is a disease in which cholestasis in liver caused by chronic nonsuppurutive destructive cholangitis of bile duct or loss of bile duct is a major pathological condition and symptoms observed based on cholestasis include fatigue, itching paraesthesia, jaundice and so forth. On the other hand, primary sclerosing cholangitis is a disease caused by inflammatory stricture of a bile duct and causes symptoms accompanying chronic cholestasis (such as fatigue and itching paraesthesia). Thus, the present invention provides drugs for diseases in which stasis of bile acids occurs in the liver due to lesion of the bile duct and which eventually leads to liver disorders.

The IBAT inhibiting compound which is used for the treatment of cholestasis-caused hepatopathy is not particularly restricted so far as it is a compound which is bonded to BAT and inhibits it. IBAT is a membrane protein which exists on the inner membrane of ileum and it recovers bile acids which are discharged in the inside of small intestine from liver through the bile duct. An inhibiting compound to IBAT is hoped as a drug for the treatment of hyperlipidemia (see The Journal of Biological Chemistry, 268, 18035-18046, 1993). IBAT inhibiting compounds are disclosed in literature such as International Patent Applications Gazette Nos. WO93/16055 and WO02/08211, and so forth. However, their effectiveness on cholestasis-caused hepatopathy, particularly their effectiveness on primary biliary cirrhosis and primary sclerosing cholangitis is not at all disclosed therein.

Examples of the IBAT inhibiting compound include 1,4-benzothiazepine derivatives, 1,5-benzothiazepine derivatives, 1,2-benzothiazepine derivatives, 1-benzothiepine derivatives, cholic acid derivatives, and lignan analogues.

Specific examples of the 1,4-benzothiazepine derivatives and 1,5-benzothiazepine derivatives as IBAT inhibiting compounds include those compounds described in International Patent Application Gazette No. WO02/08211, Published Translation of Japanese Patent Application No. Hei 10-504035, International Patent Application Gazette No. WO00/61568, and Japanese Patent Application Laid-open No. Hei 10-279568, and their salts, solvates, or derivatives having physiological functions.

Examples of the 1,2-benzothiazepine derivatives as IBAT inhibiting compounds include those compounds described in International Patent Application Gazette No. WO00/47568 and their salts, solvates, or derivatives having physiological functions. Moreover, examples of the IBAT inhibiting compounds include those compounds described in Japanese Patent No. 2839805, Japanese Patent Applications Nos. 4-277151, 5-310634, and 9-241206, International Patent Applications Gazette Nos. WO93-16055, WO94-18183, WO94-18184, WO98-38182, WO99-35135, WO99-64410, WO01-66533, WO96-16051, WO00-20437, European Patent Applications Nos. EP624593, EP624594, EP624595, EP624596, and EP489423, International Patent Application Gazette No. WO01-34570, Japanese Patent Application Laid-open No. Hei 6-321783, International Patent Applications Gazette Nos. WO00-20392, WO00-20393, WO00-20410, WO₀₂-08211, WO98-56757, WO00-35889, Japanese Patent Application Laid-open Nos. 2000-178188 and 2001-89429, and International Patent Applications Gazette Nos. WO₀₂-50051, WO03-22286, WO03-22825, WO03-22830, WO03-20710, WO03-43992, and WO03-40127, and their salts, solvates, or derivatives having physiological functions.

Further, examples of preferable IBAT inhibiting compounds include compounds described below. The compounds are merely exemplary and the present invention which relates to pharmaceutical compositions containing the IBAT inhibiting compounds which are drugs for the treatment or prevention of primary biliary cirrhosis or primary sclerosing cholangitis do not depend on specific IBAT inhibiting compounds.

1-{4-[4-(3,3-Dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetra- hydro-1,4-benzothiazepin-5-yl)phenoxymethyl]benzyl}-4aza-1- azoniabicyclo[2.2.2]octane chloride (compound A mentioned later);

Trans-3-butyl-3-ethyl-2 3,4,5-tetrahydro-7,8-dimethoxy-5-phenyl- 1,4-benzothiazepine-1,1-dioxide (compound B mentioned later);

Trans-3-butyl-3-ethyl-2,3,4,5-tetrahydro-5-phenyl-1,4-benzo- thiazepine-1,1-dioxide (compound C mentioned later);

Cis-[3-(3,3-dibutyl-7-dimethylamino-4-hydroxy-1,1-dioxo-2,3,4,5- tetrahydro-1-benzothiepin-5-yl)phenyl]trimethylammonium iodide (compound D mentioned later);

Cis-1-{4-[4-(3,3-dibutyl-7-dimethylamino-4-hydroxy-1,1-dioxo- 2,3,4,5-tetrahydro-1-benzothiepin-5-yl)phenoxymethyl]benzyl}-4-aza-1- azoniabicyclo[2.2.2]octane chloride;

Cis-{4-[3-(3,3-dibutyl-7-dimethylamino-4-hydroxy-1,1-dioxo- 2,3,4,5-tetrahydro-1-benzothiepin-5-yl)phenylcarbamoyl]butyl}triethyl- ammonium trifluoroacetate;

2,3,4,5,6-Pentahydroxyhexanoic acid [3-(3,3-dibutyl-7- dimethylamino-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1-benzothiepin- 5-yl)phenyl]amide;

2,3,4,5,6-Pentahydroxyhexanoic acid [3-(3-butyl-3-ethyl-7- dimethylamino-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1-benzothiepin- 5-yl) phenyl]amide;

5-(2,3,4,5,6-Pentahydroxyhexylamino)pentanoic acid [3-(3,3- dibutyl-7-dimethylamino-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1- benzothiepin-5-yl)phenyl]amide;

5-(2,3,4,5,6-pentahydroxyhexylamino)pentanoic acid [3-(3-butyl-3-ethyl-7-dimethylamino-4-hydroxy-1,1-dioxo-2,3,4,5- tetrahydro-1-benzothiepin-5-yl)phenyl]amide;

Methyl 1-(3,4-dimethoxyphenyl)-3-(3-ethylvaleryl)-4-hydroxy- 6,7,8-trimethoxy-2-naphthoate (compound E mentioned later);

{1-O-[4-(3,4-Dimethoxyphenyl)-2-(3-ethylpentanoyl)-5,6,7- trimethoxy-3-(methoxycarbonyl)naphthalen-1-yl]-β-D-glucopyranosido}uronic acid (compound F mentioned later);

The IBAT inhibiting compounds also include respective salts, for example acid addition salts, of 1,4-benzothiazepine derivatives, 1,5-benzothiazepine derivatives, 1,2-benzothiazepine derivatives, or 1-benzothiepine derivatives, etc. The acid addition salts are preferably pharmaceutically acceptable salts and include various known salts, for example, hydrochlorides, hydrobromides, sulfates, hydrogen sulfates, dihydrogen phosphates, citrates, maleates, tartarates, fumarates, gluconates, and methanesulfonates. The acid addition salts of IBAT inhibiting compounds are obtained by adding an equimolar amount or a few times molar amount of an acid component to the IBAT inhibiting compounds. The acid component which can be used include pharmaceutically acceptable mineral acids or organic acids, such as hydrochloric acid, hydrobromic acid, sulfuric acid, hydrogen sulfuric acid, dihydrogen phosphoric acid, citric acid, maleic acid, tartaric acid, fumaric acid, gluconic acid, and methanesulfonic acid.

It is preferable to form salts of lignan derivatives. Examples of pharmaceutically acceptable salts include salts of alkali metals such as sodium salts and potassium salts, salts of alkaline earth metals such as calcium salts and magnesium salts, quaternary ammonium salts such as tetramethylammonium salts, organic amine salts (for example, diethylamine salts), inorganic acid addition salts such as hydrochlorides and sulfates, and organic acid addition salts such as acetates, oxalates, and benzenesulfonates.

To manufacture pharmaceutical compositions which are drugs for the treatment or prevention of cholestasis-caused hepatopathy, it is preferable to optionally add a pharmaceutically acceptable carrier to an effective amount of IBAT inhibiting compound. Examples of pharmaceutically acceptable carriers include an excipient, a binder such as carboxymethyl cellulose, a disintegrating agent, a lubricant, and an additive.

When the compounds of the present invention are administered to humans, they can be administered orally in the form of a tablet, a powder, a granule, a capsule, a sugar coated tablet, a liquid, a syrup and so forth. Dosages may vary according to the age, weight, and symptom of the patient. Normally, in the case of an adult, a dosage of 0.1 mg or more, preferably 1 mg or more and as upper limits, usually 5 g or less, preferably 1 g or less, particularly preferably 500 mg or less is exemplified. The aforementioned dosage is administered at a time or in portions in a plurality of times. Administration period is as follows. Generally, the drug is administered everyday for a few weeks to a few months. However, both the dosage and administration period of the drug may be increased or decreased according to the symptom of the patient.

EXAMPLES

The present invention is further explained based on the following examples. However, the present invention is not restricted to the following examples. Thin layer chromatography (TLC) was performed using Precoated Silica Gel 60 F254 (manufactured by MERCK COMPANY) and spots were confirmed by UV (254 nm) irradiation. Measurement of nuclear magnetic resonance spectra (NMR) was carried out with AL-300 (FT-NMR manufactured by JEOL COMPANY). Chemical shifts were indicated by 6 (ppm) by use of tetramethylsilane (TMS) as an internal standard. Mass spectrum (MS) was measured by use of JMS-5X102 (manufactured by JEOL COMPANY) using fast atom bombardment mass spectrum (FAB-MS). Silica gel 60 of from 230 mesh to 400 mesh (manufactured by MERCK COMPANY) was used as a filler for silica gel column. In the operations carried out in the examples, “filtration” means filtration carried out by using a Kiriyama funnel and filter paper for the funnel (both the funnel and the filter paper are manufactured by NIPPON RIGAKU KIKAI CO., LTD.) and “concentration” means removal by evaporation of solvent or excess reagent under reduced pressure by using an evaporator (manufactured by TOKYO RIGAKU KIKAI CO., LTD.)

[Example 1] 1-{5-[3-(3,3-Dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5- tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1- azoniabicyclo[2.2.2]octane bromide Step a: Synthesis of methyl 2-benzylideneaminohexanoate

To a suspension of 7.79 g of methyl 2-aminohexanoate hydrochloride in 70 ml of dichloromethane were added 8.67 g of triethylamine (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.), 7.74 g of anhydrous magnesium sulfate, and 4.55 g of benzaldehyde and the resultant was stirred overnight at room temperature. The reaction suspension was then filtered and the filtrate was concentrated. 280 ml of ether was added to the residue and the resultant suspension was filtered and the filtrate was concentrated. Again, 280 ml of ether was added to the residue and filtration and concentration were similarly repeated to obtain 10.0 g of the title compound.

Step b: Synthesis of methyl 2-benzylideneamino-2-butylhexanoate

To a solution of 8.06 g of the compound obtained in the step a in 25 ml of DMF was added 1 .66 g of sodium hydride (60% dispersion in oil) (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.) in an argon atmosphere under ice cooling, and the resultant was stirred for 2 hours at room temperature. To the reaction suspension was dropwise added a solution of 8.90 g of 1-1odobutane in 15 ml of DMF in an argon atmosphere under ice cooling, and the mixture was stirred at room temperature for 3 hours. Under ice cooling, a solution of 5.5 g of ammonium chloride in 50 ml of water was dropwise added to the reaction suspension and then the mixture was separated by adding to it 80 ml of ether and 30 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain 10.0 g of the title compound.

Step c: Synthesis of methyl 2-amino-2-butylhexanoate

To a solution of 15.46 g of the compound obtained in the step b in 70 ml of petroleum ether was added 30 ml of 1 N hydrochloric acid, and the mixture was stirred for 1 hour at room temperature. The reaction solution was separated by adding to it 60 ml of water. The water layer was washed twice with 80 ml of ether, an aqueous solution of 5N sodium hydroxide was added to it, and pH of the solution was adjusted to 9 to 10. The water layer was separated by adding to it 160 ml of ethyl acetate and the organic layer was washed with 160 ml of saturated saline. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain 10.0 g of the title compound.

Step d: Synthesis of 2-amino-2-butylhexanol

To a suspension of 7.52 g of lithium aluminum hydride (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.) in 50 ml of THF was dropwise added a solution of 17.34 g of the compound obtained in the step c in 120 ml of THE under ice cooling and the mixture was stirred at 60° C for 1 hour. To the reaction suspension was dropwise added 25 ml of water under ice cooling. Then, 600 ml of ethyl acetate was added to the resultant at room temperature. The mixture was filtered through Celite and washed with 900 ml of ethyl acetate. The filtrate was concentrated to obtain 10.0 g of the title compound.

Step e: Synthesis of 2-amino-2-butylhexyl hydrogen sulfate

To a solution of 7.97 g of the compound obtained in the step d in 90 ml of dichioromethane was dropwise added 8.04 g of chiorosulfonic acid under ice cooling and the mixture was stirred overnight at room temperature. The reaction solution was concentrated and 90 ml of acetone-ether (1:1) was added to the residue. The mixture was allowed to stand at −20° C for 3 hours. The precipitate was filtered, washed with 300 ml of acetone-ether (1:1) to obtain 10.0 g of the title compound.

Step f: Synthesis of 4-fluoro-2-benzoylthiophenol

To a solution of 10.1 g of 2,5-difluorobenzophenone in 200 ml of DMSO was added 3.5 g of lithium sulfide (manufactured by ALDRICH CHEMICAL COMPANY) and the mixture was stirred in a nitrogen atmosphere at 1200C for 3 hours. To the reaction solution was added 200 ml of 1N hydrochloric acid under ice cooling, and further 400 ml of ethyl acetate and 200 ml of water were added to the mixture to separate it. The organic layer was washed with 400 ml of water and then with 200 ml of saturated saline. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain 10.54 g of the title compound.

Step g: Synthesis of 2- (2-amino-2-butylhexylthio)-5-fluoro- benzophenone

To a solution of 10.54 g of the compound obtained in the step f in 100 ml of butyl acetate were added 11.50 g of the compound obtained in the step e and a solution of 7.25 g of sodium hydroxide in 100 ml of water and the mixture was stirred at 90° C for 1 hour. The reaction mixture was separated by adding to it 300 ml of ethyl acetate and 300 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with chloroform-methanol-28% aqueous ammonia (50:1 :0.1) to obtain 10.09 g of the title compound.

Step h: Synthesis of 3,3-dibutyl-2, 3-dihydro-7-fluoro-5-phenyl-1 4- benzothiazepine

To a solution of 10.08 g of the compound obtained in the step g in 40m1 of 2,6-lutidine (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.) was added 0.60 g of p-toluenesulfonic acid monohydrate (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.), and the mixture was stirred at 130° C for 34 hours. The reaction solution was separated by adding to it 400 ml of ethyl acetate and 400 ml of water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (30:1) to obtain 7.87 g of the title compound.

Step i: Synthesis of 3,3-dibutyl-2,3-dihydro-7-fluoro-5-phenyl-1,4- benzothiazepine-1,1-dioxide

To a solution of 7.86 g of the compound obtained in the step h in 50 ml of dichloromethane were added 150 ml of acetonitrile, a solution of 13.3 g of sodium periodate (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.) in 70 ml of water, and 0.42 g of ruthenium trichloride (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.), and the mixture was stirred at room temperature for 24 hours. The reaction suspension was separated by adding to it 300 ml of dichloromethane and 300 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (6:1) to obtain 5.72 g of the title compound.

Step j: Synthesis of 3,3-dibutyl-2,3-dihydro-7-fluoro-5-(3-nitrophenyl)- 1,4-benzothiazepine-1,1-dioxide

To 5.32 g of the compound obtained in the step i was added a mixed solution composed of 20 ml of fuming nitric acid and 15 ml of concentrated sulfuric acid under ice cooling and the mixture was stirred at room temperature for 1 hour. The reaction mixture was dropwise added to a SN sodium hydroxide solution under ice cooling, and the mixture was separated by adding to it iSOmI of dichloromethane and 50 ml of water at room temperature. The organic layer was washed with 150 ml of saturated saline, dried over anhydrous sodium sulfate, and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (5:1) to obtain 5.48 g of the title compound.

Step k: Synthesis of 3,3-dibutyl-2,3-dihydro-7-dimethylamino-5- (3-nitrophenyl)-1,4-benzothiazepine-1,1-dioxide

To 5.48 g of the compound obtained in the step j was added 200 ml of a THF solution of 2 mol/l dimethylamine (manufactured by ALDRICH CHEMICAL COMPANY) and the mixture was heated at 55° C for 14 hours. The reaction solution was concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (2:1). The eluate was washed with 50 ml of ether to obtain 5.69 g of the title compound.

Step l: Synthesis of 3,3-dibutyl-2,3-dihydro-7-dimethylamino-5- (3-aminophenyl) -1,4-benzothiazepine-1,1-dioxide

To a solution of 5.9 g of the compound obtained in the step k in 100 ml of chloroform were added 100 ml of methanol and 1.2 g of 10% palladium-carbon (manufactured by MERCK COMPANY), and the mixture was stirred in a hydrogen atmosphere at room temperature for 4 hours. The catalyst in the reaction suspension was removed by filtering and the filtrate was concentrated. The residue was charged in a silica gel column and then eluted with chloroform-methanol (30:1) to obtain 4.38 g of the title compound.

Step m: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-dimethylamino-5- (3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

To 4.38 g of the compound obtained in the step l was added 150 ml of a THF solution of 1 mol/l borane-THF complex (manufactured by KANTO CHEMICAL COMPANY), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was dropwise added 10 ml of water under ice cooling until foaming stopped and then the reaction solution was stirred at room temperature for 1.5 hours. The mixture was then separated by adding to it 150 ml of ethyl acetate, 50 ml of water, and 100 ml of aqueous solution of 1N sodium hydroxide at room temperature. The organic layer was washed with 150 ml of water and allowed to stand at room temperature for 1.5 hours. The organic layer was dried over anhydroussodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (1:1) to obtain 3.83 g of the title compound.

Step n: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-dimethylamino-5- [3-(6-bromohexanoyl)aminophenyl]-1,4-benzothiazepine-1,1-dioxide

To a solution of 0.73 g of the compound obtained in the step m in 15 ml of dichloromethane was added 0.27 g of potassium carbonate and then 0.37 g of 6-bromo-n-caproyl chloride, and the mixture was stirred at room temperature for 20 minutes. The reaction solution was separated by adding to it 35 ml of dichioromethane and 50 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (1:1) to obtain 1.00 g of the title compound.

Step o: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-dimethylamino-5- [3-(6-bromothiohexanoyl)aminophenyl]-1,4-benzothiazepine-1,1-dioxide

To a solution of 50 mg of the compound obtained in the step n in 1.5 ml of THF was added 90 mg of Lawesson's reagent, and the mixture was stirred at room temperature for 40 hours. The reaction solution was then separated by adding to it 6 ml of ethyl acetate and 8 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (2:1) to obtain 37 mg of the title compound. Rf value 0.41 (developed with hexane:ethyl acetate=3:1).

Step p: Synthesis of 1 -{5-[3-(3,3-dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]- pentyl}-1-azoniabicyclo[2.2.2]octane bromide

To a solution of 36 mg of the compound obtained in the step o in 1 ml of acetonitrile was added 7 mg of quinuclidine (ta-287 mentioned earlier), and the mixture was heated at 50° C for 22 hours. The reaction solution was concentrated and the residue was dissolved in 0.2 ml of dichloromethane. 2 ml of ether was added to the solution and the precipitate formed was washed with 2 ml of ether to obtain 32 mg of the title compound. ¹H-NMR (CDCl₃) δ: 0.84 (3H, t); 0.90 (3H, t); 1.18-1.51 (8H, m); 1.60-2.23 (17H, m); 2.84 (6H, s); 2.95-3.12 (3H, m); 3.26-3.43 (3H, m); 3.58 (6H, t); 6.03-6.07 (2H, m); 6.47 (1H, dd); 7.34-7.39 (2H, m); 7.72-7.76 (1H, m); 7.84 (1H, d); 7.98 (1H, s); 11.56 (1H, s). MS (m/z): 667 (M+).

[Example 2] 1 -{5-[3-(3-Butyl-3-ethyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}- 1-azoniabicyclo[2.2.2]octane bromide Step a: Synthesis of 3-butyl-3-ethyl-2,3,4,5-tetrahydro-7- dimethylamino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps a to m in Example 1 was followed except that methyl 2-aminobutyrate hydrochloride was used instead of the methyl 2-aminohexanoate hydrochloride used in the step a of Example 1 to obtain the title compound.

Step b: Synthesis of 1-{5-[3-(3-butyl-3-ethyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}- 1-azoniabicyclo[2.2.2]octane bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step a in this example was used to obtain the title compound.

[Example 3] 1-{5-[3-(3,3-Dipropyl-7-dimethylamino-1,1-dioxo-2,3,4,5- tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbanmoyl]pentyl}-1- azoniabicyclo-[2.2.2]octane bromide Step a: Synthesis of 3,3-dipropyl-2,3,4,5-tetrahydro-7-dimethylamino-5- (3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps d to m in Example 1 was followed except that 2-amino-2-propylpentanoic acid (manufactured by ADVANCED CHEMTECH COMPANY) was used instead of the compound obtained in the step c in Example 1 to obtain the title compound.

Step b: Synthesis of 1-{5-[3-(3,3-dipropyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbanmoyl]- pentyl}-1-azoniabicyclo[2.2.2]octane bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step a in this example was used to obtain the title compound.

[Example 4] 1-{5-[3-(3,3-Dipentyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]- pentyl}-1-azoniabicyclo[2.2.2]octane bromide Step a: Synthesis of methyl 2-aminoheptanoate hydrochloride

To a suspension of 2.18 g of 2-aminoheptanoic acid in 50 ml of methanol was dropwise added 2.19 g of thionyl chloride (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.), and the mixture was stirred overnight at 60° C. Methanol and thionyl chloride were removed by evaporation and the residue was washed with 20 ml of ether to obtain 2.84 g of the title compound.

Step b: Synthesis of 3,3-dipentyl-2,3,4,5-tetrahydro-7-dimethylamino-5- (3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps a to m in Example 1 was followed except that the compound obtained in the step a in this example was used and that in the step b, 1-1odopentane instead of 1-1odobutane was allowed to react to obtain the title compound.

Step c: Synthesis of 1-{5-[3-(3,3-dipentyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}- 1-azoniabicyclo[2.2.2]octane bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step b in this example was used to obtain the title compound.

[Example 5] 1-{5-[3-(3,3-Dihexyl-7-dimethylamino-1,1-dioxo-2,3,4,5- tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1- azoniabicyclo[2.2.2]octane bromide Step a: Synthesis of methyl 2-aminooctanoate hydrochloride

Instead of 2-aminoheptanoic acid used in the step a in Example 4,2-aminocaprylic acid was used to obtain the title compound.

Step b: Synthesis of 3,3-dihexyl-2,3,4,5-tetrahydro-7-dimethylamino-5- (3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps a to m in Example 1 was followed except that the compound obtained in the step a in this example was used and that in the step b, 1-odohexane instead of 1-odobutane was allowed to react to obtain the title compound.

Step c: Synthesis of 1-{5-[3-(3,3-dihexyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}- 1-azoniabicyclo[2.2.2]octane bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step b in this example was used to obtain the title compound.

[Example 6] 1-{5-[3-(3,3-Dibutyl-7-diethylamino-1,1-dioxo-2,3,4,5- tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}l - azoniabicyclo[2.2.2]octane bromide Step a: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-diethylamino-5- (3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps a to m in Example 1 was followed except that in the step k, diethylamine instead of dimethylamine was allowed to react to obtain the title compound.

Step b: Synthesis of 1-{5-[3-(3,3-dibutyl-7-diethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}- 1- azoniabicyclo[2.2.2]octane bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step a in this example was used to obtain the title compound.

[Example 7] 1-{5-[3-(3,3-Dibutyl-7-ethylmethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}1-azoniabicyclo[2.2.2]octane bromide Step a: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-ethylmethyl- amino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps a to m in Example 1 was followed except that in the step k, ethylmethylamine instead of dimethylamine was allowed to react to obtain the title compound.

Step b: Synthesis of 1-{5-[3-(3,3-dibutyl-7-ethylmethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}- 1-azoniabicyclo[2.2.2]octane bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step a in this example was used to obtain the title compound.

[Example 8] 1-{5-[3-(3,3-Dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]- pentyl}-1-azoniabicyclo[2.2.2]octane bromide (an optically active form) Step a: Synthesis of 3,3-dibutyl-2, 3,4,5-tetrahydro-7-dimethylamino-5- (3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide (an optically active form)

The compound obtained in the step m in Example 1 was charged in an optical column CHIRALCEL-OJ for preparatory chromatography (manufactured by DAICEL CHEMICAL INDUSTRIES LTD., having a particle size of 10 μm, a diameter of 2 cm, and a length of 25 cm) at a flow rate of 18.9 ml/mm, and then eluted with methanol to separate the compounds into compounds of S form and R form. The retention times of the obtained optically active forms in the optical column for analysis were 7 minutes and 14 minutes, respectively. Column; CHIRALPAK-OJ (manufactured by DAICEL CHEMICAL INDUSTRIES LTD., having a particle size of 10 μm, a diameter of 0.46 cm, and a length of 25 cm), mobile phase; methanol, flow rate; 0.5 ml/mm, UV wavelength detected; 288 nm.

Step b: Synthesis of 1-{5-[3-(3,3-dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]- pentyl}-1-azoniabicyclo[2.2.2]octane bromide (an optically active form)

The procedure in the steps n to p in Example 1 was followed except that the optically active synthetic intermediate obtained in the step a in this example was used to obtain the title compound.

[Example 9] 1-(3-{3-[3,3-Dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}- propyl)-1-azoniabicyclo[2.2.2]octane bromide Step a: Synthesis of 1-(3-isothiocyanatopropyl)-1-azoniabicyclo- [2.2.2]octane bromide

To a solution of 55 mg of 3-bromopropyl isothiocyanate in 1 ml of acetonitrile was added 33 mg of quinuclidine, and the mixture was heated at 50° C for 19 hours. The reaction solution was concentrated and the residue was washed 3 times with 1 ml of ether to obtain the title compound.

Step b: Synthesis of 1-(3-{3-[3-(3,3-dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)- 1-azoniabicyclo[2.2.2]octane bromide

To a solution of 60 mg of the compound obtained in the step m in Example 1 in 1.5 ml of chloroform was added a solution of 43 mg of the compound obtained in the step a in this example in 0.5 ml of acetonitrile, and the mixture was heated at 55° C overnight. The reaction solution was concentrated and the residue was dissolved in 0.3 ml of dichloromethane. To the resultant was added 1.5 ml of ether, and the precipitate formed was washed with 2 ml of ether to obtain 77 mg of the title compound. ¹H -NMR (ODCl₃) δ: 0.84 (3H, t); 0.90 (3H, t); 1.13-1.49 (8H, m); 1.68-2.23 (13H, in); 2.84 (6H, s); 2.99 (1H, d); 3.40 (1H, d); 3.52 (6H, t); 3.59-3.75 (4H, m); 6.00 (1H, s); 6.02 (1H, d); 6.48 (1H, dd); 7.24-7.34 (2H, m); 7.46 (1H, d); 7.62 (1H, s); 7.85 (1H, d); 8.58 (1H, s), 940 (1H, s). MS (m/z) 654 (M+).

[Example 10] 1-(3-{3-[3-(3-Butyl-3-ethyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl] thioureido}propyl)- 1-azoniabicyclo[2.2.2]octane bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step a in Example 2 was used to obtain the title compound. [Example 11] 1-(3-{3-[3-(3,3-Dipropyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1- azoniabicyclo[2.2.2]octafle bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step a in Example 3 was used to obtain the title compound.

[Example 12] 1-(3-{3-[3-(3,3-Dipentyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1- azoniabicyclo[2.2.2]octane bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step b in Example 4 was used to obtain the title compound.

[Example 13] 1-(3-{3-[3-(3,3-Dihexyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1- azoniabicyclo[2.2.2]octane bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step b in Example 5 was used to obtain the title compound.

[Example 14] 1-(3-{3-[3-(3,3-Dibutyl-7-diethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1- azoniabicyclo[2.2.2]octane bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step a in Example 6 was used to obtain the title compound.

[Example 15] 1-(3-{3-[3-(3,3-Dibutyl-7-ethylmethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1- azoniabicyclo[2.2.2]octane bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step a in Example 7 was used to obtain the title compound.

[Example 16] 1-(3-{3-[3-(3,3-Dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1- azoniabicyclo[2.2.2]octane bromide (an optically active form)

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step a in Example 8 was used to obtain the title compound.

[Examples 17 to 3785, 4067 to 5404, and 5407 to 5448]

As shown in the following formulae,

the procedure in the steps a and b in Example 9 is followed except that any one of the various isothiocyanate (is-1) to (is-17) represented by the formula (5-2b), any one of various tertiary amines (ta-1) to (ta-407) represented by the formula (2), and the compound obtained in the step m in Example 1 are used to obtain compounds of Examples 17 to 3785, 4067 to 5404, and 5407 to 5448 as represented by the formula (1A) as shown in Table 2. In the formula (1A), “-sp-” indicates any one of the (sp-1) to (sp-25) and “-an” indicates any one of the (an-1) to (an-407).

TABLE 2 Reaction Compound Example reagent of Example No. is ta sp an 17 is-1 ta-1 sp-1 an-1 18 is-1 ta-2 sp-1 an-2 19 is-1 ta-3 sp-1 an-3 20 is-1 ta-4 sp-1 an-4 21 is-1 ta-5 sp-1 an-5 22 is-1 ta-6 sp-1 an-6 23 is-1 ta-7 sp-1 an-7 24 is-1 ta-8 sp-1 an-8 25 is-1 ta-9 sp-1 an-9 26 is-1 ta-10 sp-1 an-10 27 is-1 ta-11 sp-1 an-11 28 is-1 ta-12 sp-1 an-12 29 is-1 ta-13 sp-1 an-13 30 is-1 ta-14 sp-1 an-14 31 is-1 ta-15 sp-1 an-15 32 is-1 ta-16 sp-1 an-16 33 is-1 ta-17 sp-1 an-17 34 is-1 ta-18 sp-1 an-18 35 is-1 ta-19 sp-1 an-19 36 is-1 ta-20 sp-1 an-20 37 is-1 ta-21 sp-1 an-21 38 is-1 ta-22 sp-1 an-22 39 is-1 ta-23 sp-1 an-23 40 is-1 ta-24 sp-1 an-24 41 is-1 ta-25 sp-1 an-25 42 is-1 ta-26 sp-1 an-26 43 is-1 ta-27 sp-1 an-27 44 is-1 ta-28 sp-1 an-28 45 is-1 ta-29 sp-1 an-29 46 is-1 ta-30 sp-1 an-30 47 is-1 ta-31 sp-1 an-31 48 is-1 ta-32 sp-1 an-32 49 is-1 ta-33 sp-1 an-33 50 is-1 ta-34 sp-1 an-34 51 is-1 ta-35 sp-1 an-35 52 is-1 ta-36 sp-1 an-36 53 is-1 ta-37 sp-1 an-37 54 is-1 ta-38 sp-1 an-38 55 is-1 ta-39 sp-1 an-39 56 is-1 ta-40 sp-1 an-40 57 is-1 ta-41 sp-1 an-41 58 is-1 ta-42 sp-1 an-42 59 is-1 ta-43 sp-1 an-43 60 is-1 ta-44 sp-1 an-44 61 is-1 ta-45 sp-1 an-45 62 is-1 ta-46 sp-1 an-46 63 is-1 ta-47 sp-1 an-47 64 is-1 ta-48 sp-1 an-48 65 is-1 ta-49 sp-1 an-49 66 is-1 ta-50 sp-1 an-50 67 is-1 ta-51 sp-1 an-51 68 is-1 ta-52 sp-1 an-52 69 is-1 ta-53 sp-1 an-53 70 is-1 ta-54 sp-1 an-54 71 is-1 ta-55 sp-1 an-55 72 is-1 ta-56 sp-1 an-56 73 is-1 ta-57 sp-1 an-57 74 is-1 ta-58 sp-1 an-58 75 is-1 ta-59 sp-1 an-59 76 is-1 ta-60 sp-1 an-60 77 is-1 ta-61 sp-1 an-61 78 is-1 ta-62 sp-1 an-62 79 is-1 ta-63 sp-1 an-63 80 is-1 ta-64 sp-1 an-64 81 is-1 ta-65 sp-1 an-65 82 is-1 ta-66 sp-1 an-66 83 is-1 ta-67 sp-1 an-67 84 is-1 ta-68 sp-1 an-68 85 is-1 ta-69 sp-1 an-69 86 is-1 ta-70 sp-1 an-70 87 is-1 ta-71 sp-1 an-71 88 is-1 ta-72 sp-1 an-72 89 is-1 ta-73 sp-1 an-73 90 is-1 ta-74 sp-1 an-74 91 is-1 ta-75 sp-1 an-75 92 is-1 ta-76 sp-1 an-76 93 is-1 ta-77 sp-1 an-77 94 is-1 ta-78 sp-1 an-78 95 is-1 ta-79 sp-1 an-79 96 is-1 ta-80 sp-1 an-80 97 is-1 ta-81 sp-1 an-81 98 is-1 ta-82 sp-1 an-82 99 is-1 ta-83 sp-1 an-83 100 is-1 ta-84 sp-1 an-84 101 is-1 ta-85 sp-1 an-85 102 is-1 ta-86 sp-1 an-86 103 is-1 ta-87 sp-1 an-87 104 is-1 ta-88 sp-1 an-88 105 is-1 ta-89 sp-1 an-89 106 is-1 ta-90 sp-1 an-90 107 is-1 ta-91 sp-1 an-91 108 is-1 ta-92 sp-1 an-92 109 is-1 ta-93 sp-1 an-93 110 is-1 ta-94 sp-1 an-94 111 is-1 ta-95 sp-1 an-95 112 is-1 ta-96 sp-1 an-96 113 is-1 ta-97 sp-1 an-97 114 is-1 ta-98 sp-1 an-98 115 is-1 ta-99 sp-1 an-99 116 is-1 ta-100 sp-1 an-100 117 is-1 ta-101 sp-1 an-101 118 is-1 ta-102 sp-1 an-102 119 is-1 ta-103 sp-1 an-103 120 is-1 ta-104 sp-1 an-104 121 is-1 ta-105 sp-1 an-105 122 is-1 ta-106 sp-1 an-106 123 is-1 ta-107 sp-1 an-107 124 is-1 ta-108 sp-1 an-108 125 is-1 ta-109 sp-1 an-109 126 is-1 ta-110 sp-1 an-110 127 is-1 ta-111 sp-1 an-111 128 is-1 ta-112 sp-1 an-112 129 is-1 ta-113 sp-1 an-113 130 is-1 ta-114 sp-1 an-114 131 is-1 ta-115 sp-1 an-115 132 is-1 ta-116 sp-1 an-116 133 is-1 ta-117 sp-1 an-117 134 is-1 ta-118 sp-1 an-118 135 is-1 ta-119 sp-1 an-119 136 is-1 ta-120 sp-1 an-120 137 is-1 ta-121 sp-1 an-121 138 is-1 ta-122 sp-1 an-122 139 is-1 ta-123 sp-1 an-123 140 is-1 ta-124 sp-1 an-124 141 is-1 ta-125 sp-1 an-125 142 is-1 ta-126 sp-1 an-126 143 is-1 ta-127 sp-1 an-127 144 is-1 ta-128 sp-1 an-128 145 is-1 ta-129 sp-1 an-129 146 is-1 ta-130 sp-1 an-130 147 is-1 ta-131 sp-1 an-131 148 is-1 ta-132 sp-1 an-132 149 is-1 ta-133 sp-1 an-133 150 is-1 ta-134 sp-1 an-134 151 is-1 ta-135 sp-1 an-135 152 is-1 ta-136 sp-1 an-136 153 is-1 ta-137 sp-1 an-137 154 is-1 ta-138 sp-1 an-138 155 is-1 ta-139 sp-1 an-139 156 is-1 ta-140 sp-1 an-140 157 is-1 ta-141 sp-1 an-141 158 is-1 ta-142 sp-1 an-142 159 is-1 ta-143 sp-1 an-143 160 is-1 ta-144 sp-1 an-144 161 is-1 ta-145 sp-1 an-145 162 is-1 ta-146 sp-1 an-146 163 is-1 ta-147 sp-1 an-147 164 is-1 ta-148 sp-1 an-148 165 is-1 ta-149 sp-1 an-149 166 is-1 ta-150 sp-1 an-150 167 is-1 ta-151 sp-1 an-151 168 is-1 ta-152 sp-1 an-152 169 is-1 ta-153 sp-1 an-153 170 is-1 ta-154 sp-1 an-154 171 is-1 ta-155 sp-1 an-155 172 is-1 ta-156 sp-1 an-156 173 is-1 ta-157 sp-1 an-157 174 is-1 ta-158 sp-1 an-158 175 is-1 ta-159 sp-1 an-159 176 is-1 ta-160 sp-1 an-160 177 is-1 ta-161 sp-1 an-161 178 is-1 ta-162 sp-1 an-162 179 is-1 ta-163 sp-1 an-163 180 is-1 ta-164 sp-1 an-164 181 is-1 ta-165 sp-1 an-165 182 is-1 ta-166 sp-1 an-166 183 is-1 ta-167 sp-1 an-167 184 is-1 ta-168 sp-1 an-168 185 is-1 ta-169 sp-1 an-169 186 is-1 ta-170 sp-1 an-170 187 is-1 ta-171 sp-1 an-171 188 is-1 ta-172 sp-1 an-172 189 is-1 ta-173 sp-1 an-173 190 is-1 ta-174 sp-1 an-174 191 is-1 ta-175 sp-1 an-175 192 is-1 ta-176 sp-1 an-176 193 is-1 ta-177 sp-1 an-177 194 is-1 ta-178 sp-1 an-178 195 is-1 ta-179 sp-1 an-179 196 is-1 ta-180 sp-1 an-180 197 is-1 ta-181 sp-1 an-181 198 is-1 ta-182 sp-1 an-182 199 is-1 ta-183 sp-1 an-183 200 is-1 ta-184 sp-1 an-184 201 is-1 ta-185 sp-1 an-185 202 is-1 ta-186 sp-1 an-186 203 is-1 ta-187 sp-1 an-187 204 is-1 ta-188 sp-1 an-188 205 is-1 ta-189 sp-1 an-189 206 is-1 ta-190 sp-1 an-190 207 is-1 ta-191 sp-1 an-191 208 is-1 ta-192 sp-1 an-192 209 is-1 ta-193 sp-1 an-193 210 is-1 ta-194 sp-1 an-194 211 is-1 ta-195 sp-1 an-195 212 is-1 ta-196 sp-1 an-196 213 is-1 ta-197 sp-1 an-197 214 is-1 ta-198 sp-1 an-198 215 is-1 ta-199 sp-1 an-199 216 is-1 ta-200 sp-1 an-200 217 is-1 ta-201 sp-1 an-201 218 is-1 ta-202 sp-1 an-202 219 is-1 ta-203 sp-1 an-203 220 is-1 ta-204 sp-1 an-204 221 is-1 ta-205 sp-1 an-205 222 is-1 ta-206 sp-1 an-206 223 is-1 ta-207 sp-1 an-207 224 is-1 ta-208 sp-1 an-208 225 is-1 ta-209 sp-1 an-209 226 is-1 ta-210 sp-1 an-210 227 is-1 ta-211 sp-1 an-211 228 is-1 ta-212 sp-1 an-212 229 is-1 ta-213 sp-1 an-213 230 is-1 ta-214 sp-1 an-214 231 is-1 ta-215 sp-1 an-215 232 is-1 ta-216 sp-1 an-216 233 is-1 ta-217 sp-1 an-217 234 is-1 ta-218 sp-1 an-218 235 is-1 ta-219 sp-1 an-219 236 is-1 ta-220 sp-1 an-220 237 is-1 ta-221 sp-1 an-221 238 is-1 ta-222 sp-1 an-222 239 is-1 ta-223 sp-1 an-223 240 is-1 ta-224 sp-1 an-224 241 is-1 ta-225 sp-1 an-225 242 is-1 ta-226 sp-1 an-226 243 is-1 ta-227 sp-1 an-227 244 is-1 ta-228 sp-1 an-228 245 is-1 ta-229 sp-1 an-229 246 is-1 ta-230 sp-1 an-230 247 is-1 ta-231 sp-1 an-231 248 is-1 ta-232 sp-1 an-232 249 is-1 ta-233 sp-1 an-233 250 is-1 ta-234 sp-1 an-234 251 is-1 ta-235 sp-1 an-235 252 is-1 ta-236 sp-1 an-236 253 is-1 ta-237 sp-1 an-237 254 is-1 ta-238 sp-1 an-238 255 is-1 ta-239 sp-1 an-239 256 is-1 ta-240 sp-1 an-240 257 is-1 ta-241 sp-1 an-241 258 is-1 ta-242 sp-1 an-242 259 is-1 ta-243 sp-1 an-243 260 is-1 ta-244 sp-1 an-244 261 is-1 ta-245 sp-1 an-245 262 is-1 ta-246 sp-1 an-246 263 is-1 ta-247 sp-1 an-247 264 is-1 ta-248 sp-1 an-248 265 is-1 ta-249 sp-1 an-249 266 is-1 ta-250 sp-1 an-250 267 is-1 ta-251 sp-1 an-251 268 is-1 ta-252 sp-1 an-252 269 is-1 ta-253 sp-1 an-253 270 is-1 ta-254 sp-1 an-254 271 is-1 ta-255 sp-1 an-255 272 is-1 ta-256 sp-1 an-256 273 is-1 ta-257 sp-1 an-257 274 is-1 ta-258 sp-1 an-258 275 is-1 ta-259 sp-1 an-259 276 is-1 ta-260 sp-1 an-260 277 is-1 ta-261 sp-1 an-261 278 is-1 ta-262 sp-1 an-262 279 is-1 ta-263 sp-1 an-263 280 is-1 ta-264 sp-1 an-264 281 is-1 ta-265 sp-1 an-265 282 is-1 ta-266 sp-1 an-266 283 is-1 ta-267 sp-1 an-267 284 is-1 ta-268 sp-1 an-268 285 is-1 ta-269 sp-1 an-269 286 is-1 ta-270 sp-1 an-270 287 is-1 ta-271 sp-1 an-271 288 is-1 ta-272 sp-1 an-272 289 is-1 ta-273 sp-1 an-273 290 is-1 ta-274 sp-1 an-274 291 is-1 ta-275 sp-1 an-275 292 is-1 ta-276 sp-1 an-276 293 is-1 ta-277 sp-1 an-277 294 is-1 ta-278 sp-1 an-278 295 is-1 ta-279 sp-1 an-279 296 is-1 ta-280 sp-1 an-280 297 is-1 ta-281 sp-1 an-281 298 is-1 ta-282 sp-1 an-282 299 is-1 ta-283 sp-1 an-283 300 is-1 ta-284 sp-1 an-284 301 is-1 ta-285 sp-1 an-285 302 is-1 ta-286 sp-1 an-286 303 is-1 ta-287 sp-1 an-287 304 is-1 ta-288 sp-1 an-288 305 is-1 ta-289 sp-1 an-289 306 is-1 ta-290 sp-1 an-290 307 is-1 ta-291 sp-1 an-291 308 is-1 ta-292 sp-1 an-292 309 is-1 ta-293 sp-1 an-293 310 is-1 ta-294 sp-1 an-294 311 is-1 ta-295 sp-1 an-295 312 is-1 ta-296 sp-1 an-296 313 is-1 ta-297 sp-1 an-297 314 is-1 ta-298 sp-1 an-298 315 is-1 ta-299 sp-1 an-299 316 is-1 ta-300 sp-1 an-300 317 is-1 ta-301 sp-1 an-301 318 is-1 ta-302 sp-1 an-302 319 is-1 ta-303 sp-1 an-303 320 is-1 ta-304 sp-1 an-304 321 is-1 ta-305 sp-1 an-305 322 is-1 ta-306 sp-1 an-306 323 is-1 ta-307 sp-1 an-307 324 is-1 ta-308 sp-1 an-308 325 is-1 ta-309 sp-1 an-309 326 is-1 ta-310 sp-1 an-310 327 is-1 ta-311 sp-1 an-311 328 is-1 ta-312 sp-1 an-312 329 is-1 ta-313 sp-1 an-313 330 is-1 ta-314 sp-1 an-314 331 is-1 ta-315 sp-1 an-315 332 is-1 ta-316 sp-1 an-316 333 is-1 ta-317 sp-1 an-317 334 is-1 ta-318 sp-1 an-318 335 is-1 ta-319 sp-1 an-319 336 is-1 ta-320 sp-1 an-320 337 is-1 ta-321 sp-1 an-321 338 is-1 ta-322 sp-1 an-322 339 is-1 ta-323 sp-1 an-323 340 is-1 ta-324 sp-1 an-324 341 is-1 ta-325 sp-1 an-325 342 is-1 ta-326 sp-1 an-326 343 is-1 ta-327 sp-1 an-327 344 is-1 ta-328 sp-1 an-328 345 is-1 ta-329 sp-1 an-329 346 is-1 ta-330 sp-1 an-330 347 is-1 ta-331 sp-1 an-331 348 is-1 ta-332 sp-1 an-332 349 is-1 ta-333 sp-1 an-333 350 is-1 ta-334 sp-1 an-334 351 is-1 ta-335 sp-1 an-335 352 is-1 ta-336 sp-1 an-336 353 is-1 ta-337 sp-1 an-337 354 is-1 ta-338 sp-1 an-338 355 is-1 ta-339 sp-1 an-339 356 is-1 ta-340 sp-1 an-340 357 is-1 ta-341 sp-1 an-341 358 is-1 ta-342 sp-1 an-342 359 is-1 ta-343 sp-1 an-343 360 is-1 ta-344 sp-1 an-344 361 is-1 ta-345 sp-1 an-345 362 is-1 ta-346 sp-1 an-346 363 is-1 ta-347 sp-1 an-347 364 is-1 ta-348 sp-1 an-348 365 is-1 ta-349 sp-1 an-349 366 is-1 ta-350 sp-1 an-350 367 is-1 ta-351 sp-1 an-351 368 is-1 ta-352 sp-1 an-352 369 is-1 ta-353 sp-1 an-353 370 is-1 ta-354 sp-1 an-354 371 is-1 ta-355 sp-1 an-355 372 is-1 ta-356 sp-1 an-356 373 is-1 ta-357 sp-1 an-357 374 is-1 ta-358 sp-1 an-358 375 is-1 ta-359 sp-1 an-359 376 is-1 ta-360 sp-1 an-360 377 is-1 ta-361 sp-1 an-361 378 is-1 ta-362 sp-1 an-362 379 is-1 ta-363 sp-1 an-363 380 is-1 ta-364 sp-1 an-364 381 is-1 ta-365 sp-1 an-365 382 is-1 ta-366 sp-1 an-366 383 is-1 ta-367 sp-1 an-367 384 is-1 ta-368 sp-1 an-368 385 is-1 ta-369 sp-1 an-369 386 is-1 ta-370 sp-1 an-370 387 is-1 ta-371 sp-1 an-371 388 is-1 ta-372 sp-1 an-372 389 is-1 ta-373 sp-1 an-373 390 is-1 ta-374 sp-1 an-374 391 is-1 ta-375 sp-1 an-375 392 is-1 ta-376 sp-1 an-376 393 is-1 ta-377 sp-1 an-377 394 is-2 ta-1 sp-2 an-1 395 is-2 ta-2 sp-2 an-2 396 is-2 ta-3 sp-2 an-3 397 is-2 ta-4 sp-2 an-4 398 is-2 ta-5 sp-2 an-5 399 is-2 ta-6 sp-2 an-6 400 is-2 ta-7 sp-2 an-7 401 is-2 ta-8 sp-2 an-8 402 is-2 ta-9 sp-2 an-9 403 is-2 ta-10 sp-2 an-10 404 is-2 ta-11 sp-2 an-11 405 is-2 ta-12 sp-2 an-12 406 is-2 ta-13 sp-2 an-13 407 is-2 ta-14 sp-2 an-14 408 is-2 ta-15 sp-2 an-15 409 is-2 ta-16 sp-2 an-16 410 is-2 ta-17 sp-2 an-17 411 is-2 ta-18 sp-2 an-18 412 is-2 ta-19 sp-2 an-19 413 is-2 ta-20 sp-2 an-20 414 is-2 ta-21 sp-2 an-21 415 is-2 ta-22 sp-2 an-22 416 is-2 ta-23 sp-2 an-23 417 is-2 ta-24 sp-2 an-24 418 is-2 ta-25 sp-2 an-25 419 is-2 ta-26 sp-2 an-26 420 is-2 ta-27 sp-2 an-27 421 is-2 ta-28 sp-2 an-28 422 is-2 ta-29 sp-2 an-29 423 is-2 ta-30 sp-2 an-30 424 is-2 ta-31 sp-2 an-31 425 is-2 ta-32 sp-2 an-32 426 is-2 ta-33 sp-2 an-33 427 is-2 ta-34 sp-2 an-34 428 is-2 ta-35 sp-2 an-35 429 is-2 ta-36 sp-2 an-36 430 is-2 ta-37 sp-2 an-37 431 is-2 ta-38 sp-2 an-38 432 is-2 ta-39 sp-2 an-39 433 is-2 ta-40 sp-2 an-40 434 is-2 ta-41 sp-2 an-41 435 is-2 ta-42 sp-2 an-42 436 is-2 ta-43 sp-2 an-43 437 is-2 ta-44 sp-2 an-44 438 is-2 ta-45 sp-2 an-45 439 is-2 ta-46 sp-2 an-46 440 is-2 ta-47 sp-2 an-47 441 is-2 ta-48 sp-2 an-48 442 is-2 ta-49 sp-2 an-49 443 is-2 ta-50 sp-2 an-50 444 is-2 ta-51 sp-2 an-51 445 is-2 ta-52 sp-2 an-52 446 is-2 ta-53 sp-2 an-53 447 is-2 ta-54 sp-2 an-54 448 is-2 ta-55 sp-2 an-55 449 is-2 ta-56 sp-2 an-56 450 is-2 ta-57 sp-2 an-57 451 is-2 ta-58 sp-2 an-58 452 is-2 ta-59 sp-2 an-59 453 is-2 ta-60 sp-2 an-60 454 is-2 ta-61 sp-2 an-61 455 is-2 ta-62 sp-2 an-62 456 is-2 ta-63 sp-2 an-63 457 is-2 ta-64 sp-2 an-64 458 is-2 ta-65 sp-2 an-65 459 is-2 ta-66 sp-2 an-66 460 is-2 ta-67 sp-2 an-67 461 is-2 ta-68 sp-2 an-68 462 is-2 ta-69 sp-2 an-69 463 is-2 ta-70 sp-2 an-70 464 is-2 ta-71 sp-2 an-71 465 is-2 ta-72 sp-2 an-72 466 is-2 ta-73 sp-2 an-73 467 is-2 ta-74 sp-2 an-74 468 is-2 ta-75 sp-2 an-75 469 is-2 ta-76 sp-2 an-76 470 is-2 ta-77 sp-2 an-77 471 is-2 ta-78 sp-2 an-78 472 is-2 ta-79 sp-2 an-79 473 is-2 ta-80 sp-2 an-80 474 is-2 ta-81 sp-2 an-81 475 is-2 ta-82 sp-2 an-82 476 is-2 ta-83 sp-2 an-83 477 is-2 ta-84 sp-2 an-84 478 is-2 ta-85 sp-2 an-85 479 is-2 ta-86 sp-2 an-86 480 is-2 ta-87 sp-2 an-87 481 is-2 ta-88 sp-2 an-88 482 is-2 ta-89 sp-2 an-89 483 is-2 ta-90 sp-2 an-90 484 is-2 ta-91 sp-2 an-91 485 is-2 ta-92 sp-2 an-92 486 is-2 ta-93 sp-2 an-93 487 is-2 ta-94 sp-2 an-94 488 is-2 ta-95 sp-2 an-95 489 is-2 ta-96 sp-2 an-96 490 is-2 ta-97 sp-2 an-97 491 is-2 ta-98 sp-2 an-98 492 is-2 ta-99 sp-2 an-99 493 is-2 ta-100 sp-2 an-100 494 is-2 ta-101 sp-2 an-101 495 is-2 ta-102 sp-2 an-102 496 is-2 ta-103 sp-2 an-103 497 is-2 ta-104 sp-2 an-104 498 is-2 ta-105 sp-2 an-105 499 is-2 ta-106 sp-2 an-106 500 is-2 ta-107 sp-2 an-107 501 is-2 ta-108 sp-2 an-108 502 is-2 ta-109 sp-2 an-109 503 is-2 ta-110 sp-2 an-110 504 is-2 ta-111 sp-2 an-111 505 is-2 ta-112 sp-2 an-112 506 is-2 ta-113 sp-2 an-113 507 is-2 ta-114 sp-2 an-114 508 is-2 ta-115 sp-2 an-115 509 is-2 ta-116 sp-2 an-116 510 is-2 ta-117 sp-2 an-117 511 is-2 ta-118 sp-2 an-118 512 is-2 ta-119 sp-2 an-119 513 is-2 ta-120 sp-2 an-120 514 is-2 ta-121 sp-2 an-121 515 is-2 ta-122 sp-2 an-122 516 is-2 ta-123 sp-2 an-123 517 is-2 ta-124 sp-2 an-124 518 is-2 ta-125 sp-2 an-125 519 is-2 ta-126 sp-2 an-126 520 is-2 ta-127 sp-2 an-127 521 is-2 ta-128 sp-2 an-128 522 is-2 ta-129 sp-2 an-129 523 is-2 ta-130 sp-2 an-130 524 is-2 ta-131 sp-2 an-131 525 is-2 ta-132 sp-2 an-132 526 is-2 ta-133 sp-2 an-133 527 is-2 ta-134 sp-2 an-134 528 is-2 ta-135 sp-2 an-135 529 is-2 ta-136 sp-2 an-136 530 is-2 ta-137 sp-2 an-137 531 is-2 ta-138 sp-2 an-138 532 is-2 ta-139 sp-2 an-139 533 is-2 ta-140 sp-2 an-140 534 is-2 ta-141 sp-2 an-141 535 is-2 ta-142 sp-2 an-142 536 is-2 ta-143 sp-2 an-143 537 is-2 ta-144 sp-2 an-144 538 is-2 ta-145 sp-2 an-145 539 is-2 ta-146 sp-2 an-146 540 is-2 ta-147 sp-2 an-147 541 is-2 ta-148 sp-2 an-148 542 is-2 ta-149 sp-2 an-149 543 is-2 ta-150 sp-2 an-150 544 is-2 ta-151 sp-2 an-151 545 is-2 ta-152 sp-2 an-152 546 is-2 ta-153 sp-2 an-153 547 is-2 ta-154 sp-2 an-154 548 is-2 ta-155 sp-2 an-155 549 is-2 ta-156 sp-2 an-156 550 is-2 ta-157 sp-2 an-157 551 is-2 ta-158 sp-2 an-158 552 is-2 ta-159 sp-2 an-159 553 is-2 ta-160 sp-2 an-160 554 is-2 ta-161 sp-2 an-161 555 is-2 ta-162 sp-2 an-162 556 is-2 ta-163 sp-2 an-163 557 is-2 ta-164 sp-2 an-164 558 is-2 ta-165 sp-2 an-165 559 is-2 ta-166 sp-2 an-166 560 is-2 ta-167 sp-2 an-167 561 is-2 ta-168 sp-2 an-168 562 is-2 ta-169 sp-2 an-169 563 is-2 ta-170 sp-2 an-170 564 is-2 ta-171 sp-2 an-171 565 is-2 ta-172 sp-2 an-172 566 is-2 ta-173 sp-2 an-173 567 is-2 ta-174 sp-2 an-174 568 is-2 ta-175 sp-2 an-175 569 is-2 ta-176 sp-2 an-176 570 is-2 ta-177 sp-2 an-177 571 is-2 ta-178 sp-2 an-178 572 is-2 ta-179 sp-2 an-179 573 is-2 ta-180 sp-2 an-180 574 is-2 ta-181 sp-2 an-181 575 is-2 ta-182 sp-2 an-182 576 is-2 ta-183 sp-2 an-183 577 is-2 ta-184 sp-2 an-184 578 is-2 ta-185 sp-2 an-185 579 is-2 ta-186 sp-2 an-186 580 is-2 ta-187 sp-2 an-187 581 is-2 ta-188 sp-2 an-188 582 is-2 ta-189 sp-2 an-189 583 is-2 ta-190 sp-2 an-190 584 is-2 ta-191 sp-2 an-191 585 is-2 ta-192 sp-2 an-192 586 is-2 ta-193 sp-2 an-193 587 is-2 ta-194 sp-2 an-194 588 is-2 ta-195 sp-2 an-195 589 is-2 ta-196 sp-2 an-196 590 is-2 ta-197 sp-2 an-197 591 is-2 ta-198 sp-2 an-198 592 is-2 ta-199 sp-2 an-199 593 is-2 ta-200 sp-2 an-200 594 is-2 ta-201 sp-2 an-201 595 is-2 ta-202 sp-2 an-202 596 is-2 ta-203 sp-2 an-203 597 is-2 ta-204 sp-2 an-204 598 is-2 ta-205 sp-2 an-205 599 is-2 ta-206 sp-2 an-206 600 is-2 ta-207 sp-2 an-207 601 is-2 ta-208 sp-2 an-208 602 is-2 ta-209 sp-2 an-209 603 is-2 ta-210 sp-2 an-210 604 is-2 ta-211 sp-2 an-211 605 is-2 ta-212 sp-2 an-212 606 is-2 ta-213 sp-2 an-213 607 is-2 ta-214 sp-2 an-214 608 is-2 ta-215 sp-2 an-215 609 is-2 ta-216 sp-2 an-216 610 is-2 ta-217 sp-2 an-217 611 is-2 ta-218 sp-2 an-218 612 is-2 ta-219 sp-2 an-219 613 is-2 ta-220 sp-2 an-220 614 is-2 ta-221 sp-2 an-221 615 is-2 ta-222 sp-2 an-222 616 is-2 ta-223 sp-2 an-223 617 is-2 ta-224 sp-2 an-224 618 is-2 ta-225 sp-2 an-225 619 is-2 ta-226 sp-2 an-226 620 is-2 ta-227 sp-2 an-227 621 is-2 ta-228 sp-2 an-228 622 is-2 ta-229 sp-2 an-229 623 is-2 ta-230 sp-2 an-230 624 is-2 ta-231 sp-2 an-231 625 is-2 ta-232 sp-2 an-232 626 is-2 ta-233 sp-2 an-233 627 is-2 ta-234 sp-2 an-234 628 is-2 ta-235 sp-2 an-235 629 is-2 ta-236 sp-2 an-236 630 is-2 ta-237 sp-2 an-237 631 is-2 ta-238 sp-2 an-238 632 is-2 ta-239 sp-2 an-239 633 is-2 ta-240 sp-2 an-240 634 is-2 ta-241 sp-2 an-241 635 is-2 ta-242 sp-2 an-242 636 is-2 ta-243 sp-2 an-243 637 is-2 ta-244 sp-2 an-244 638 is-2 ta-245 sp-2 an-245 639 is-2 ta-246 sp-2 an-246 640 is-2 ta-247 sp-2 an-247 641 is-2 ta-248 sp-2 an-248 642 is-2 ta-249 sp-2 an-249 643 is-2 ta-250 sp-2 an-250 644 is-2 ta-251 sp-2 an-251 645 is-2 ta-252 sp-2 an-252 646 is-2 ta-253 sp-2 an-253 647 is-2 ta-254 sp-2 an-254 648 is-2 ta-255 sp-2 an-255 649 is-2 ta-256 sp-2 an-256 650 is-2 ta-257 sp-2 an-257 651 is-2 ta-258 sp-2 an-258 652 is-2 ta-259 sp-2 an-259 653 is-2 ta-260 sp-2 an-260 654 is-2 ta-261 sp-2 an-261 655 is-2 ta-262 sp-2 an-262 656 is-2 ta-263 sp-2 an-263 657 is-2 ta-264 sp-2 an-264 658 is-2 ta-265 sp-2 an-265 659 is-2 ta-266 sp-2 an-266 660 is-2 ta-267 sp-2 an-267 661 is-2 ta-268 sp-2 an-268 662 is-2 ta-269 sp-2 an-269 663 is-2 ta-270 sp-2 an-270 664 is-2 ta-271 sp-2 an-271 665 is-2 ta-272 sp-2 an-272 666 is-2 ta-273 sp-2 an-273 667 is-2 ta-274 sp-2 an-274 668 is-2 ta-275 sp-2 an-275 669 is-2 ta-276 sp-2 an-276 670 is-2 ta-277 sp-2 an-277 671 is-2 ta-278 sp-2 an-278 672 is-2 ta-279 sp-2 an-279 673 is-2 ta-280 sp-2 an-280 674 is-2 ta-281 sp-2 an-281 675 is-2 ta-282 sp-2 an-282 676 is-2 ta-283 sp-2 an-283 677 is-2 ta-284 sp-2 an-284 678 is-2 ta-285 sp-2 an-285 679 is-2 ta-286 sp-2 an-286 9 is-2 ta-287 sp-2 an-287 680 is-2 ta-288 sp-2 an-288 681 is-2 ta-289 sp-2 an-289 682 is-2 ta-290 sp-2 an-290 683 is-2 ta-291 sp-2 an-291 684 is-2 ta-292 sp-2 an-292 685 is-2 ta-293 sp-2 an-293 686 is-2 ta-294 sp-2 an-294 687 is-2 ta-295 sp-2 an-295 688 is-2 ta-296 sp-2 an-296 689 is-2 ta-297 sp-2 an-297 690 is-2 ta-298 sp-2 an-298 691 is-2 ta-299 sp-2 an-299 692 is-2 ta-300 sp-2 an-300 693 is-2 ta-301 sp-2 an-301 694 is-2 ta-302 sp-2 an-302 695 is-2 ta-303 sp-2 an-303 696 is-2 ta-304 sp-2 an-304 697 is-2 ta-305 sp-2 an-305 698 is-2 ta-306 sp-2 an-306 699 is-2 ta-307 sp-2 an-307 700 is-2 ta-308 sp-2 an-308 701 is-2 ta-309 sp-2 an-309 702 is-2 ta-310 sp-2 an-310 703 is-2 ta-311 sp-2 an-311 704 is-2 ta-312 sp-2 an-312 705 is-2 ta-313 sp-2 an-313 706 is-2 ta-314 sp-2 an-314 707 is-2 ta-315 sp-2 an-315 708 is-2 ta-316 sp-2 an-316 709 is-2 ta-317 sp-2 an-317 710 is-2 ta-318 sp-2 an-318 711 is-2 ta-319 sp-2 an-319 712 is-2 ta-320 sp-2 an-320 713 is-2 ta-321 sp-2 an-321 714 is-2 ta-322 sp-2 an-322 715 is-2 ta-323 sp-2 an-323 716 is-2 ta-324 sp-2 an-324 717 is-2 ta-325 sp-2 an-325 718 is-2 ta-326 sp-2 an-326 719 is-2 ta-327 sp-2 an-327 720 is-2 ta-328 sp-2 an-328 721 is-2 ta-329 sp-2 an-329 722 is-2 ta-330 sp-2 an-330 723 is-2 ta-331 sp-2 an-331 724 is-2 ta-332 sp-2 an-332 725 is-2 ta-333 sp-2 an-333 726 is-2 ta-334 sp-2 an-334 727 is-2 ta-335 sp-2 an-335 728 is-2 ta-336 sp-2 an-336 729 is-2 ta-337 sp-2 an-337 730 is-2 ta-338 sp-2 an-338 731 is-2 ta-339 sp-2 an-339 732 is-2 ta-340 sp-2 an-340 733 is-2 ta-341 sp-2 an-341 734 is-2 ta-342 sp-2 an-342 735 is-2 ta-343 sp-2 an-343 736 is-2 ta-344 sp-2 an-344 737 is-2 ta-345 sp-2 an-345 738 is-2 ta-346 sp-2 an-346 739 is-2 ta-347 sp-2 an-347 740 is-2 ta-348 sp-2 an-348 741 is-2 ta-349 sp-2 an-349 742 is-2 ta-350 sp-2 an-350 743 is-2 ta-351 sp-2 an-351 744 is-2 ta-352 sp-2 an-352 745 is-2 ta-353 sp-2 an-353 746 is-2 ta-354 sp-2 an-354 747 is-2 ta-355 sp-2 an-355 748 is-2 ta-356 sp-2 an-356 749 is-2 ta-357 sp-2 an-357 750 is-2 ta-358 sp-2 an-358 751 is-2 ta-359 sp-2 an-359 752 is-2 ta-360 sp-2 an-360 753 is-2 ta-361 sp-2 an-361 754 is-2 ta-362 sp-2 an-362 755 is-2 ta-363 sp-2 an-363 756 is-2 ta-364 sp-2 an-364 757 is-2 ta-365 sp-2 an-365 758 is-2 ta-366 sp-2 an-366 759 is-2 ta-367 sp-2 an-367 760 is-2 ta-368 sp-2 an-368 761 is-2 ta-369 sp-2 an-369 762 is-2 ta-370 sp-2 an-370 763 is-2 ta-371 sp-2 an-371 764 is-2 ta-372 sp-2 an-372 765 is-2 ta-373 sp-2 an-373 766 is-2 ta-374 sp-2 an-374 767 is-2 ta-375 sp-2 an-375 768 is-2 ta-376 sp-2 an-376 769 is-2 ta-377 sp-2 an-377 770 is-3 ta-1 sp-3 an-1 771 is-3 ta-2 sp-3 an-2 772 is-3 ta-3 sp-3 an-3 773 is-3 ta-4 sp-3 an-4 774 is-3 ta-5 sp-3 an-5 775 is-3 ta-6 sp-3 an-6 776 is-3 ta-7 sp-3 an-7 777 is-3 ta-8 sp-3 an-8 778 is-3 ta-9 sp-3 an-9 779 is-3 ta-10 sp-3 an-10 780 is-3 ta-11 sp-3 an-11 781 is-3 ta-12 sp-3 an-12 782 is-3 ta-13 sp-3 an-13 783 is-3 ta-14 sp-3 an-14 784 is-3 ta-15 sp-3 an-15 785 is-3 ta-16 sp-3 an-16 786 is-3 ta-17 sp-3 an-17 787 is-3 ta-18 sp-3 an-18 788 is-3 ta-19 sp-3 an-19 789 is-3 ta-20 sp-3 an-20 790 is-3 ta-21 sp-3 an-21 791 is-3 ta-22 sp-3 an-22 792 is-3 ta-23 sp-3 an-23 793 is-3 ta-24 sp-3 an-24 794 is-3 ta-25 sp-3 an-25 795 is-3 ta-26 sp-3 an-26 796 is-3 ta-27 sp-3 an-27 797 is-3 ta-28 sp-3 an-28 798 is-3 ta-29 sp-3 an-29 799 is-3 ta-30 sp-3 an-30 800 is-3 ta-31 sp-3 an-31 801 is-3 ta-32 sp-3 an-32 802 is-3 ta-33 sp-3 an-33 803 is-3 ta-34 sp-3 an-34 804 is-3 ta-35 sp-3 an-35 805 is-3 ta-36 sp-3 an-36 806 is-3 ta-37 sp-3 an-37 807 is-3 ta-38 sp-3 an-38 808 is-3 ta-39 sp-3 an-39 809 is-3 ta-40 sp-3 an-40 810 is-3 ta-41 sp-3 an-41 811 is-3 ta-42 sp-3 an-42 812 is-3 ta-43 sp-3 an-43 813 is-3 ta-44 sp-3 an-44 814 is-3 ta-45 sp-3 an-45 815 is-3 ta-46 sp-3 an-46 816 is-3 ta-47 sp-3 an-47 817 is-3 ta-48 sp-3 an-48 818 is-3 ta-49 sp-3 an-49 819 is-3 ta-50 sp-3 an-50 820 is-3 ta-51 sp-3 an-51 821 is-3 ta-52 sp-3 an-52 822 is-3 ta-53 sp-3 an-53 823 is-3 ta-54 sp-3 an-54 824 is-3 ta-55 sp-3 an-55 825 is-3 ta-56 sp-3 an-56 826 is-3 ta-57 sp-3 an-57 827 is-3 ta-58 sp-3 an-58 828 is-3 ta-59 sp-3 an-59 829 is-3 ta-60 sp-3 an-60 830 is-3 ta-61 sp-3 an-61 831 is-3 ta-62 sp-3 an-62 832 is-3 ta-63 sp-3 an-63 833 is-3 ta-64 sp-3 an-64 834 is-3 ta-65 sp-3 an-65 835 is-3 ta-66 sp-3 an-66 836 is-3 ta-67 sp-3 an-67 837 is-3 ta-68 sp-3 an-68 838 is-3 ta-69 sp-3 an-69 839 is-3 ta-70 sp-3 an-70 840 is-3 ta-71 sp-3 an-71 841 is-3 ta-72 sp-3 an-72 842 is-3 ta-73 sp-3 an-73 843 is-3 ta-74 sp-3 an-74 844 is-3 ta-75 sp-3 an-75 845 is-3 ta-76 sp-3 an-76 846 is-3 ta-77 sp-3 an-77 847 is-3 ta-78 sp-3 an-78 848 is-3 ta-79 sp-3 an-79 849 is-3 ta-80 sp-3 an-80 850 is-3 ta-81 sp-3 an-81 851 is-3 ta-82 sp-3 an-82 852 is-3 ta-83 sp-3 an-83 853 is-3 ta-84 sp-3 an-84 854 is-3 ta-85 sp-3 an-85 855 is-3 ta-86 sp-3 an-86 856 is-3 ta-87 sp-3 an-87 857 is-3 ta-88 sp-3 an-88 858 is-3 ta-89 sp-3 an-89 859 is-3 ta-90 sp-3 an-90 860 is-3 ta-91 sp-3 an-91 861 is-3 ta-92 sp-3 an-92 862 is-3 ta-93 sp-3 an-93 863 is-3 ta-94 sp-3 an-94 864 is-3 ta-95 sp-3 an-95 865 is-3 ta-96 sp-3 an-96 866 is-3 ta-97 sp-3 an-97 867 is-3 ta-98 sp-3 an-98 868 is-3 ta-99 sp-3 an-99 869 is-3 ta-100 sp-3 an-100 870 is-3 ta-101 sp-3 an-101 871 is-3 ta-102 sp-3 an-102 872 is-3 ta-103 sp-3 an-103 873 is-3 ta-104 sp-3 an-104 874 is-3 ta-105 sp-3 an-105 875 is-3 ta-106 sp-3 an-106 876 is-3 ta-107 sp-3 an-107 877 is-3 ta-108 sp-3 an-108 878 is-3 ta-109 sp-3 an-109 879 is-3 ta-110 sp-3 an-110 880 is-3 ta-111 sp-3 an-111 881 is-3 ta-112 sp-3 an-112 882 is-3 ta-113 sp-3 an-113 883 is-3 ta-114 sp-3 an-114 884 is-3 ta-115 sp-3 an-115 885 is-3 ta-116 sp-3 an-116 886 is-3 ta-117 sp-3 an-117 887 is-3 ta-118 sp-3 an-118 888 is-3 ta-119 sp-3 an-119 889 is-3 ta-120 sp-3 an-120 890 is-3 ta-121 sp-3 an-121 891 is-3 ta-122 sp-3 an-122 892 is-3 ta-123 sp-3 an-123 893 is-3 ta-124 sp-3 an-124 894 is-3 ta-125 sp-3 an-125 895 is-3 ta-126 sp-3 an-126 896 is-3 ta-127 sp-3 an-127 897 is-3 ta-128 sp-3 an-128 898 is-3 ta-129 sp-3 an-129 899 is-3 ta-130 sp-3 an-130 900 is-3 ta-131 sp-3 an-131 901 is-3 ta-132 sp-3 an-132 902 is-3 ta-133 sp-3 an-133 903 is-3 ta-134 sp-3 an-134 904 is-3 ta-135 sp-3 an-135 905 is-3 ta-136 sp-3 an-136 906 is-3 ta-137 sp-3 an-137 907 is-3 ta-138 sp-3 an-138 908 is-3 ta-139 sp-3 an-139 909 is-3 ta-140 sp-3 an-140 910 is-3 ta-141 sp-3 an-141 911 is-3 ta-142 sp-3 an-142 912 is-3 ta-143 sp-3 an-143 913 is-3 ta-144 sp-3 an-144 914 is-3 ta-145 sp-3 an-145 915 is-3 ta-146 sp-3 an-146 916 is-3 ta-147 sp-3 an-147 917 is-3 ta-148 sp-3 an-148 918 is-3 ta-149 sp-3 an-149 919 is-3 ta-150 sp-3 an-150 920 is-3 ta-151 sp-3 an-151 921 is-3 ta-152 sp-3 an-152 922 is-3 ta-153 sp-3 an-153 923 is-3 ta-154 sp-3 an-154 924 is-3 ta-155 sp-3 an-155 925 is-3 ta-156 sp-3 an-156 926 is-3 ta-157 sp-3 an-157 927 is-3 ta-158 sp-3 an-158 928 is-3 ta-159 sp-3 an-159 929 is-3 ta-160 sp-3 an-160 930 is-3 ta-161 sp-3 an-161 931 is-3 ta-162 sp-3 an-162 932 is-3 ta-163 sp-3 an-163 933 is-3 ta-164 sp-3 an-164 934 is-3 ta-165 sp-3 an-165 935 is-3 ta-166 sp-3 an-166 936 is-3 ta-167 sp-3 an-167 937 is-3 ta-168 sp-3 an-168 938 is-3 ta-169 sp-3 an-169 939 is-3 ta-170 sp-3 an-170 940 is-3 ta-171 sp-3 an-171 941 is-3 ta-172 sp-3 an-172 942 is-3 ta-173 sp-3 an-173 943 is-3 ta-174 sp-3 an-174 944 is-3 ta-175 sp-3 an-175 945 is-3 ta-176 sp-3 an-176 946 is-3 ta-177 sp-3 an-177 947 is-3 ta-178 sp-3 an-178 948 is-3 ta-179 sp-3 an-179 949 is-3 ta-180 sp-3 an-180 950 is-3 ta-181 sp-3 an-181 951 is-3 ta-182 sp-3 an-182 952 is-3 ta-183 sp-3 an-183 953 is-3 ta-184 sp-3 an-184 954 is-3 ta-185 sp-3 an-185 955 is-3 ta-186 sp-3 an-186 956 is-3 ta-187 sp-3 an-187 957 is-3 ta-188 sp-3 an-188 958 is-3 ta-189 sp-3 an-189 959 is-3 ta-190 sp-3 an-190 960 is-3 ta-191 sp-3 an-191 961 is-3 ta-192 sp-3 an-192 962 is-3 ta-193 sp-3 an-193 963 is-3 ta-194 sp-3 an-194 964 is-3 ta-195 sp-3 an-195 965 is-3 ta-196 sp-3 an-196 966 is-3 ta-197 sp-3 an-197 967 is-3 ta-198 sp-3 an-198 968 is-3 ta-199 sp-3 an-199 969 is-3 ta-200 sp-3 an-200 970 is-3 ta-201 sp-3 an-201 971 is-3 ta-202 sp-3 an-202 972 is-3 ta-203 sp-3 an-203 973 is-3 ta-204 sp-3 an-204 974 is-3 ta-205 sp-3 an-205 975 is-3 ta-206 sp-3 an-206 976 is-3 ta-207 sp-3 an-207 977 is-3 ta-208 sp-3 an-208 978 is-3 ta-209 sp-3 an-209 979 is-3 ta-210 sp-3 an-210 980 is-3 ta-211 sp-3 an-211 981 is-3 ta-212 sp-3 an-212 982 is-3 ta-213 sp-3 an-213 983 is-3 ta-214 sp-3 an-214 984 is-3 ta-215 sp-3 an-215 985 is-3 ta-216 sp-3 an-216 986 is-3 ta-217 sp-3 an-217 987 is-3 ta-218 sp-3 an-218 988 is-3 ta-219 sp-3 an-219 989 is-3 ta-220 sp-3 an-220 990 is-3 ta-221 sp-3 an-221 991 is-3 ta-222 sp-3 an-222 992 is-3 ta-223 sp-3 an-223 993 is-3 ta-224 sp-3 an-224 994 is-3 ta-225 sp-3 an-225 995 is-3 ta-226 sp-3 an-226 996 is-3 ta-227 sp-3 an-227 997 is-3 ta-228 sp-3 an-228 998 is-3 ta-229 sp-3 an-229 999 is-3 ta-230 sp-3 an-230 1000 is-3 ta-231 sp-3 an-231 1001 is-3 ta-232 sp-3 an-232 1002 is-3 ta-233 sp-3 an-233 1003 is-3 ta-234 sp-3 an-234 1004 is-3 ta-235 sp-3 an-235 1005 is-3 ta-236 sp-3 an-236 1006 is-3 ta-237 sp-3 an-237 1007 is-3 ta-238 sp-3 an-238 1008 is-3 ta-239 sp-3 an-239 1009 is-3 ta-240 sp-3 an-240 1010 is-3 ta-241 sp-3 an-241 1011 is-3 ta-242 sp-3 an-242 1012 is-3 ta-243 sp-3 an-243 1013 is-3 ta-244 sp-3 an-244 1014 is-3 ta-245 sp-3 an-245 1015 is-3 ta-246 sp-3 an-246 1016 is-3 ta-247 sp-3 an-247 1017 is-3 ta-248 sp-3 an-248 1018 is-3 ta-249 sp-3 an-249 1019 is-3 ta-250 sp-3 an-250 1020 is-3 ta-251 sp-3 an-251 1021 is-3 ta-252 sp-3 an-252 1022 is-3 ta-253 sp-3 an-253 1023 is-3 ta-254 sp-3 an-254 1024 is-3 ta-255 sp-3 an-255 1025 is-3 ta-256 sp-3 an-256 1026 is-3 ta-257 sp-3 an-257 1027 is-3 ta-258 sp-3 an-258 1028 is-3 ta-259 sp-3 an-259 1029 is-3 ta-260 sp-3 an-260 1030 is-3 ta-261 sp-3 an-261 1031 is-3 ta-262 sp-3 an-262 1032 is-3 ta-263 sp-3 an-263 1033 is-3 ta-264 sp-3 an-264 1034 is-3 ta-265 sp-3 an-265 1035 is-3 ta-266 sp-3 an-266 1036 is-3 ta-267 sp-3 an-267 1037 is-3 ta-268 sp-3 an-268 1038 is-3 ta-269 sp-3 an-269 1039 is-3 ta-270 sp-3 an-270 1040 is-3 ta-271 sp-3 an-271 1041 is-3 ta-272 sp-3 an-272 1042 is-3 ta-273 sp-3 an-273 1043 is-3 ta-274 sp-3 an-274 1044 is-3 ta-275 sp-3 an-275 1045 is-3 ta-276 sp-3 an-276 1046 is-3 ta-277 sp-3 an-277 1047 is-3 ta-278 sp-3 an-278 1048 is-3 ta-279 sp-3 an-279 1049 is-3 ta-280 sp-3 an-280 1050 is-3 ta-281 sp-3 an-281 1051 is-3 ta-282 sp-3 an-282 1052 is-3 ta-283 sp-3 an-283 1053 is-3 ta-284 sp-3 an-284 1054 is-3 ta-285 sp-3 an-285 1055 is-3 ta-286 sp-3 an-286 1056 is-3 ta-287 sp-3 an-287 1057 is-3 ta-288 sp-3 an-288 1058 is-3 ta-289 sp-3 an-289 1059 is-3 ta-290 sp-3 an-290 1060 is-3 ta-291 sp-3 an-291 1061 is-3 ta-292 sp-3 an-292 1062 is-3 ta-293 sp-3 an-293 1063 is-3 ta-294 sp-3 an-294 1064 is-3 ta-295 sp-3 an-295 1065 is-3 ta-296 sp-3 an-296 1066 is-3 ta-297 sp-3 an-297 1067 is-3 ta-298 sp-3 an-298 1068 is-3 ta-299 sp-3 an-299 1069 is-3 ta-300 sp-3 an-300 1070 is-3 ta-301 sp-3 an-301 1071 is-3 ta-302 sp-3 an-302 1072 is-3 ta-303 sp-3 an-303 1073 is-3 ta-304 sp-3 an-304 1074 is-3 ta-305 sp-3 an-305 1075 is-3 ta-306 sp-3 an-306 1076 is-3 ta-307 sp-3 an-307 1077 is-3 ta-308 sp-3 an-308 1078 is-3 ta-309 sp-3 an-309 1079 is-3 ta-310 sp-3 an-310 1080 is-3 ta-311 sp-3 an-311 1081 is-3 ta-312 sp-3 an-312 1082 is-3 ta-313 sp-3 an-313 1083 is-3 ta-314 sp-3 an-314 1084 is-3 ta-315 sp-3 an-315 1085 is-3 ta-316 sp-3 an-316 1086 is-3 ta-317 sp-3 an-317 1087 is-3 ta-318 sp-3 an-318 1088 is-3 ta-319 sp-3 an-319 1089 is-3 ta-320 sp-3 an-320 1090 is-3 ta-321 sp-3 an-321 1091 is-3 ta-322 sp-3 an-322 1092 is-3 ta-323 sp-3 an-323 1093 is-3 ta-324 sp-3 an-324 1094 is-3 ta-325 sp-3 an-325 1095 is-3 ta-326 sp-3 an-326 1096 is-3 ta-327 sp-3 an-327 1097 is-3 ta-328 sp-3 an-328 1098 is-3 ta-329 sp-3 an-329 1099 is-3 ta-330 sp-3 an-330 1100 is-3 ta-331 sp-3 an-331 1101 is-3 ta-332 sp-3 an-332 1102 is-3 ta-333 sp-3 an-333 1103 is-3 ta-334 sp-3 an-334 1104 is-3 ta-335 sp-3 an-335 1105 is-3 ta-336 sp-3 an-336 1106 is-3 ta-337 sp-3 an-337 1107 is-3 ta-338 sp-3 an-338 1108 is-3 ta-339 sp-3 an-339 1109 is-3 ta-340 sp-3 an-340 1110 is-3 ta-341 sp-3 an-341 1111 is-3 ta-342 sp-3 an-342 1112 is-3 ta-343 sp-3 an-343 1113 is-3 ta-344 sp-3 an-344 1114 is-3 ta-345 sp-3 an-345 1115 is-3 ta-346 sp-3 an-346 1116 is-3 ta-347 sp-3 an-347 1117 is-3 ta-348 sp-3 an-348 1118 is-3 ta-349 sp-3 an-349 1119 is-3 ta-350 sp-3 an-350 1120 is-3 ta-351 sp-3 an-351 1121 is-3 ta-352 sp-3 an-352 1122 is-3 ta-353 sp-3 an-353 1123 is-3 ta-354 sp-3 an-354 1124 is-3 ta-355 sp-3 an-355 1125 is-3 ta-356 sp-3 an-356 1126 is-3 ta-357 sp-3 an-357 1127 is-3 ta-358 sp-3 an-358 1128 is-3 ta-359 sp-3 an-359 1129 is-3 ta-360 sp-3 an-360 1130 is-3 ta-361 sp-3 an-361 1131 is-3 ta-362 sp-3 an-362 1132 is-3 ta-363 sp-3 an-363 1133 is-3 ta-364 sp-3 an-364 1134 is-3 ta-365 sp-3 an-365 1135 is-3 ta-366 sp-3 an-366 1136 is-3 ta-367 sp-3 an-367 1137 is-3 ta-368 sp-3 an-368 1138 is-3 ta-369 sp-3 an-369 1139 is-3 ta-370 sp-3 an-370 1140 is-3 ta-371 sp-3 an-371 1141 is-3 ta-372 sp-3 an-372 1142 is-3 ta-373 sp-3 an-373 1143 is-3 ta-374 sp-3 an-374 1144 is-3 ta-375 sp-3 an-375 1145 is-3 ta-376 sp-3 an-376 1146 is-3 ta-377 sp-3 an-377 1147 is-4 ta-1 sp-4 an-1 1148 is-4 ta-2 sp-4 an-2 1149 is-4 ta-3 sp-4 an-3 1150 is-4 ta-4 sp-4 an-4 1151 is-4 ta-5 sp-4 an-5 1152 is-4 ta-6 sp-4 an-6 1153 is-4 ta-7 sp-4 an-7 1154 is-4 ta-8 sp-4 an-8 1155 is-4 ta-9 sp-4 an-9 1156 is-4 ta-10 sp-4 an-10 1157 is-4 ta-11 sp-4 an-11 1158 is-4 ta-12 sp-4 an-12 1159 is-4 ta-13 sp-4 an-13 1160 is-4 ta-14 sp-4 an-14 1161 is-4 ta-15 sp-4 an-15 1162 is-4 ta-16 sp-4 an-16 1163 is-4 ta-17 sp-4 an-17 1164 is-4 ta-18 sp-4 an-18 1165 is-4 ta-19 sp-4 an-19 1166 is-4 ta-20 sp-4 an-20 1167 is-4 ta-21 sp-4 an-21 1168 is-4 ta-22 sp-4 an-22 1169 is-4 ta-23 sp-4 an-23 1170 is-4 ta-24 sp-4 an-24 1171 is-4 ta-25 sp-4 an-25 1172 is-4 ta-26 sp-4 an-26 1173 is-4 ta-27 sp-4 an-27 1174 is-4 ta-28 sp-4 an-28 1175 is-4 ta-29 sp-4 an-29 1176 is-4 ta-30 sp-4 an-30 1177 is-4 ta-31 sp-4 an-31 1178 is-4 ta-32 sp-4 an-32 1179 is-4 ta-33 sp-4 an-33 1180 is-4 ta-34 sp-4 an-34 1181 is-4 ta-35 sp-4 an-35 1182 is-4 ta-36 sp-4 an-36 1183 is-4 ta-37 sp-4 an-37 1184 is-4 ta-38 sp-4 an-38 1185 is-4 ta-39 sp-4 an-39 1186 is-4 ta-40 sp-4 an-40 1187 is-4 ta-41 sp-4 an-41 1188 is-4 ta-42 sp-4 an-42 1189 is-4 ta-43 sp-4 an-43 1190 is-4 ta-44 sp-4 an-44 1191 is-4 ta-45 sp-4 an-45 1192 is-4 ta-46 sp-4 an-46 1193 is-4 ta-47 sp-4 an-47 1194 is-4 ta-48 sp-4 an-48 1195 is-4 ta-49 sp-4 an-49 1196 is-4 ta-50 sp-4 an-50 1197 is-4 ta-51 sp-4 an-51 1198 is-4 ta-52 sp-4 an-52 1199 is-4 ta-53 sp-4 an-53 1200 is-4 ta-54 sp-4 an-54 1201 is-4 ta-55 sp-4 an-55 1202 is-4 ta-56 sp-4 an-56 1203 is-4 ta-57 sp-4 an-57 1204 is-4 ta-58 sp-4 an-58 1205 is-4 ta-59 sp-4 an-59 1206 is-4 ta-60 sp-4 an-60 1207 is-4 ta-61 sp-4 an-61 1208 is-4 ta-62 sp-4 an-62 1209 is-4 ta-63 sp-4 an-63 1210 is-4 ta-64 sp-4 an-64 1211 is-4 ta-65 sp-4 an-65 1212 is-4 ta-66 sp-4 an-66 1213 is-4 ta-67 sp-4 an-67 1214 is-4 ta-68 sp-4 an-68 1215 is-4 ta-69 sp-4 an-69 1216 is-4 ta-70 sp-4 an-70 1217 is-4 ta-71 sp-4 an-71 1218 is-4 ta-72 sp-4 an-72 1219 is-4 ta-73 sp-4 an-73 1220 is-4 ta-74 sp-4 an-74 1221 is-4 ta-75 sp-4 an-75 1222 is-4 ta-76 sp-4 an-76 1223 is-4 ta-77 sp-4 an-77 1224 is-4 ta-78 sp-4 an-78 1225 is-4 ta-79 sp-4 an-79 1226 is-4 ta-80 sp-4 an-80 1227 is-4 ta-81 sp-4 an-81 1228 is-4 ta-82 sp-4 an-82 1229 is-4 ta-83 sp-4 an-83 1230 is-4 ta-84 sp-4 an-84 1231 is-4 ta-85 sp-4 an-85 1232 is-4 ta-86 sp-4 an-86 1233 is-4 ta-87 sp-4 an-87 1234 is-4 ta-88 sp-4 an-88 1235 is-4 ta-89 sp-4 an-89 1236 is-4 ta-90 sp-4 an-90 1237 is-4 ta-91 sp-4 an-91 1238 is-4 ta-92 sp-4 an-92 1239 is-4 ta-93 sp-4 an-93 1240 is-4 ta-94 sp-4 an-94 1241 is-4 ta-95 sp-4 an-95 1242 is-4 ta-96 sp-4 an-96 1243 is-4 ta-97 sp-4 an-97 1244 is-4 ta-98 sp-4 an-98 1245 is-4 ta-99 sp-4 an-99 1246 is-4 ta-100 sp-4 an-100 1247 is-4 ta-101 sp-4 an-101 1248 is-4 ta-102 sp-4 an-102 1249 is-4 ta-103 sp-4 an-103 1250 is-4 ta-104 sp-4 an-104 1251 is-4 ta-105 sp-4 an-105 1252 is-4 ta-106 sp-4 an-106 1253 is-4 ta-107 sp-4 an-107 1254 is-4 ta-108 sp-4 an-108 1255 is-4 ta-109 sp-4 an-109 1256 is-4 ta-110 sp-4 an-110 1257 is-4 ta-111 sp-4 an-111 1258 is-4 ta-112 sp-4 an-112 1259 is-4 ta-113 sp-4 an-113 1260 is-4 ta-114 sp-4 an-114 1261 is-4 ta-115 sp-4 an-115 1262 is-4 ta-116 sp-4 an-116 1263 is-4 ta-117 sp-4 an-117 1264 is-4 ta-118 sp-4 an-118 1265 is-4 ta-119 sp-4 an-119 1266 is-4 ta-120 sp-4 an-120 1267 is-4 ta-121 sp-4 an-121 1268 is-4 ta-122 sp-4 an-122 1269 is-4 ta-123 sp-4 an-123 1270 is-4 ta-124 sp-4 an-124 1271 is-4 ta-125 sp-4 an-125 1272 is-4 ta-126 sp-4 an-126 1273 is-4 ta-127 sp-4 an-127 1274 is-4 ta-128 sp-4 an-128 1275 is-4 ta-129 sp-4 an-129 1276 is-4 ta-130 sp-4 an-130 1277 is-4 ta-131 sp-4 an-131 1278 is-4 ta-132 sp-4 an-132 1279 is-4 ta-133 sp-4 an-133 1280 is-4 ta-134 sp-4 an-134 1281 is-4 ta-135 sp-4 an-135 1282 is-4 ta-136 sp-4 an-136 1283 is-4 ta-137 sp-4 an-137 1284 is-4 ta-138 sp-4 an-138 1285 is-4 ta-139 sp-4 an-139 1286 is-4 ta-140 sp-4 an-140 1287 is-4 ta-141 sp-4 an-141 1288 is-4 ta-142 sp-4 an-142 1289 is-4 ta-143 sp-4 an-143 1290 is-4 ta-144 sp-4 an-144 1291 is-4 ta-145 sp-4 an-145 1292 is-4 ta-146 sp-4 an-146 1293 is-4 ta-147 sp-4 an-147 1294 is-4 ta-148 sp-4 an-148 1295 is-4 ta-149 sp-4 an-149 1296 is-4 ta-150 sp-4 an-150 1297 is-4 ta-151 sp-4 an-151 1298 is-4 ta-152 sp-4 an-152 1299 is-4 ta-153 sp-4 an-153 1300 is-4 ta-154 sp-4 an-154 1301 is-4 ta-155 sp-4 an-155 1302 is-4 ta-156 sp-4 an-156 1303 is-4 ta-157 sp-4 an-157 1304 is-4 ta-158 sp-4 an-158 1305 is-4 ta-159 sp-4 an-159 1306 is-4 ta-160 sp-4 an-160 1307 is-4 ta-161 sp-4 an-161 1308 is-4 ta-162 sp-4 an-162 1309 is-4 ta-163 sp-4 an-163 1310 is-4 ta-164 sp-4 an-164 1311 is-4 ta-165 sp-4 an-165 1312 is-4 ta-166 sp-4 an-166 1313 is-4 ta-167 sp-4 an-167 1314 is-4 ta-168 sp-4 an-168 1315 is-4 ta-169 sp-4 an-169 1316 is-4 ta-170 sp-4 an-170 1317 is-4 ta-171 sp-4 an-171 1318 is-4 ta-172 sp-4 an-172 1319 is-4 ta-173 sp-4 an-173 1320 is-4 ta-174 sp-4 an-174 1321 is-4 ta-175 sp-4 an-175 1322 is-4 ta-176 sp-4 an-176 1323 is-4 ta-177 sp-4 an-177 1324 is-4 ta-178 sp-4 an-178 1325 is-4 ta-179 sp-4 an-179 1326 is-4 ta-180 sp-4 an-180 1327 is-4 ta-181 sp-4 an-181 1328 is-4 ta-182 sp-4 an-182 1329 is-4 ta-183 sp-4 an-183 1330 is-4 ta-184 sp-4 an-184 1331 is-4 ta-185 sp-4 an-185 1332 is-4 ta-186 sp-4 an-186 1333 is-4 ta-187 sp-4 an-187 1334 is-4 ta-188 sp-4 an-188 1335 is-4 ta-189 sp-4 an-189 1336 is-4 ta-190 sp-4 an-190 1337 is-4 ta-191 sp-4 an-191 1338 is-4 ta-192 sp-4 an-192 1339 is-4 ta-193 sp-4 an-193 1340 is-4 ta-194 sp-4 an-194 1341 is-4 ta-195 sp-4 an-195 1342 is-4 ta-196 sp-4 an-196 1343 is-4 ta-197 sp-4 an-197 1344 is-4 ta-198 sp-4 an-198 1345 is-4 ta-199 sp-4 an-199 1346 is-4 ta-200 sp-4 an-200 1347 is-4 ta-201 sp-4 an-201 1348 is-4 ta-202 sp-4 an-202 1349 is-4 ta-203 sp-4 an-203 1350 is-4 ta-204 sp-4 an-204 1351 is-4 ta-205 sp-4 an-205 1352 is-4 ta-206 sp-4 an-206 1353 is-4 ta-207 sp-4 an-207 1354 is-4 ta-208 sp-4 an-208 1355 is-4 ta-209 sp-4 an-209 1356 is-4 ta-210 sp-4 an-210 1357 is-4 ta-211 sp-4 an-211 1358 is-4 ta-212 sp-4 an-212 1359 is-4 ta-213 sp-4 an-213 1360 is-4 ta-214 sp-4 an-214 1361 is-4 ta-215 sp-4 an-215 1362 is-4 ta-216 sp-4 an-216 1363 is-4 ta-217 sp-4 an-217 1364 is-4 ta-218 sp-4 an-218 1365 is-4 ta-219 sp-4 an-219 1366 is-4 ta-220 sp-4 an-220 1367 is-4 ta-221 sp-4 an-221 1368 is-4 ta-222 sp-4 an-222 1369 is-4 ta-223 sp-4 an-223 1370 is-4 ta-224 sp-4 an-224 1371 is-4 ta-225 sp-4 an-225 1372 is-4 ta-226 sp-4 an-226 1373 is-4 ta-227 sp-4 an-227 1374 is-4 ta-228 sp-4 an-228 1375 is-4 ta-229 sp-4 an-229 1376 is-4 ta-230 sp-4 an-230 1377 is-4 ta-231 sp-4 an-231 1378 is-4 ta-232 sp-4 an-232 1379 is-4 ta-233 sp-4 an-233 1380 is-4 ta-234 sp-4 an-234 1381 is-4 ta-235 sp-4 an-235 1382 is-4 ta-236 sp-4 an-236 1383 is-4 ta-237 sp-4 an-237 1384 is-4 ta-238 sp-4 an-238 1385 is-4 ta-239 sp-4 an-239 1386 is-4 ta-240 sp-4 an-240 1387 is-4 ta-241 sp-4 an-241 1388 is-4 ta-242 sp-4 an-242 1389 is-4 ta-243 sp-4 an-243 1390 is-4 ta-244 sp-4 an-244 1391 is-4 ta-245 sp-4 an-245 1392 is-4 ta-246 sp-4 an-246 1393 is-4 ta-247 sp-4 an-247 1394 is-4 ta-248 sp-4 an-248 1395 is-4 ta-249 sp-4 an-249 1396 is-4 ta-250 sp-4 an-250 1397 is-4 ta-251 sp-4 an-251 1398 is-4 ta-252 sp-4 an-252 1399 is-4 ta-253 sp-4 an-253 1400 is-4 ta-254 sp-4 an-254 1401 is-4 ta-255 sp-4 an-255 1402 is-4 ta-256 sp-4 an-256 1403 is-4 ta-257 sp-4 an-257 1404 is-4 ta-258 sp-4 an-258 1405 is-4 ta-259 sp-4 an-259 1406 is-4 ta-260 sp-4 an-260 1407 is-4 ta-261 sp-4 an-261 1408 is-4 ta-262 sp-4 an-262 1409 is-4 ta-263 sp-4 an-263 1410 is-4 ta-264 sp-4 an-264 1411 is-4 ta-265 sp-4 an-265 1412 is-4 ta-266 sp-4 an-266 1413 is-4 ta-267 sp-4 an-267 1414 is-4 ta-268 sp-4 an-268 1415 is-4 ta-269 sp-4 an-269 1416 is-4 ta-270 sp-4 an-270 1417 is-4 ta-271 sp-4 an-271 1418 is-4 ta-272 sp-4 an-272 1419 is-4 ta-273 sp-4 an-273 1420 is-4 ta-274 sp-4 an-274 1421 is-4 ta-275 sp-4 an-275 1422 is-4 ta-276 sp-4 an-276 1423 is-4 ta-277 sp-4 an-277 1424 is-4 ta-278 sp-4 an-278 1425 is-4 ta-279 sp-4 an-279 1426 is-4 ta-280 sp-4 an-280 1427 is-4 ta-281 sp-4 an-281 1428 is-4 ta-282 sp-4 an-282 1429 is-4 ta-283 sp-4 an-283 1430 is-4 ta-284 sp-4 an-284 1431 is-4 ta-285 sp-4 an-285 1432 is-4 ta-286 sp-4 an-286 1433 is-4 ta-287 sp-4 an-287 1434 is-4 ta-288 sp-4 an-288 1435 is-4 ta-289 sp-4 an-289 1436 is-4 ta-290 sp-4 an-290 1437 is-4 ta-291 sp-4 an-291 1438 is-4 ta-292 sp-4 an-292 1439 is-4 ta-293 sp-4 an-293 1440 is-4 ta-294 sp-4 an-294 1441 is-4 ta-295 sp-4 an-295 1442 is-4 ta-296 sp-4 an-296 1443 is-4 ta-297 sp-4 an-297 1444 is-4 ta-298 sp-4 an-298 1445 is-4 ta-299 sp-4 an-299 1446 is-4 ta-300 sp-4 an-300 1447 is-4 ta-301 sp-4 an-301 1448 is-4 ta-302 sp-4 an-302 1449 is-4 ta-303 sp-4 an-303 1450 is-4 ta-304 sp-4 an-304 1451 is-4 ta-305 sp-4 an-305 1452 is-4 ta-306 sp-4 an-306 1453 is-4 ta-307 sp-4 an-307 1454 is-4 ta-308 sp-4 an-308 1455 is-4 ta-309 sp-4 an-309 1456 is-4 ta-310 sp-4 an-310 1457 is-4 ta-311 sp-4 an-311 1458 is-4 ta-312 sp-4 an-312 1459 is-4 ta-313 sp-4 an-313 1460 is-4 ta-314 sp-4 an-314 1461 is-4 ta-315 sp-4 an-315 1462 is-4 ta-316 sp-4 an-316 1463 is-4 ta-317 sp-4 an-317 1464 is-4 ta-318 sp-4 an-318 1465 is-4 ta-319 sp-4 an-319 1466 is-4 ta-320 sp-4 an-320 1467 is-4 ta-321 sp-4 an-321 1468 is-4 ta-322 sp-4 an-322 1469 is-4 ta-323 sp-4 an-323 1470 is-4 ta-324 sp-4 an-324 1471 is-4 ta-325 sp-4 an-325 1472 is-4 ta-326 sp-4 an-326 1473 is-4 ta-327 sp-4 an-327 1474 is-4 ta-328 sp-4 an-328 1475 is-4 ta-329 sp-4 an-329 1476 is-4 ta-330 sp-4 an-330 1477 is-4 ta-331 sp-4 an-331 1478 is-4 ta-332 sp-4 an-332 1479 is-4 ta-333 sp-4 an-333 1480 is-4 ta-334 sp-4 an-334 1481 is-4 ta-335 sp-4 an-335 1482 is-4 ta-336 sp-4 an-336 1483 is-4 ta-337 sp-4 an-337 1484 is-4 ta-338 sp-4 an-338 1485 is-4 ta-339 sp-4 an-339 1486 is-4 ta-340 sp-4 an-340 1487 is-4 ta-341 sp-4 an-341 1488 is-4 ta-342 sp-4 an-342 1489 is-4 ta-343 sp-4 an-343 1490 is-4 ta-344 sp-4 an-344 1491 is-4 ta-345 sp-4 an-345 1492 is-4 ta-346 sp-4 an-346 1493 is-4 ta-347 sp-4 an-347 1494 is-4 ta-348 sp-4 an-348 1495 is-4 ta-349 sp-4 an-349 1496 is-4 ta-350 sp-4 an-350 1497 is-4 ta-351 sp-4 an-351 1498 is-4 ta-352 sp-4 an-352 1499 is-4 ta-353 sp-4 an-353 1500 is-4 ta-354 sp-4 an-354 1501 is-4 ta-355 sp-4 an-355 1502 is-4 ta-356 sp-4 an-356 1503 is-4 ta-357 sp-4 an-357 1504 is-4 ta-358 sp-4 an-358 1505 is-4 ta-359 sp-4 an-359 1506 is-4 ta-360 sp-4 an-360 1507 is-4 ta-361 sp-4 an-361 1508 is-4 ta-362 sp-4 an-362 1509 is-4 ta-363 sp-4 an-363 1510 is-4 ta-364 sp-4 an-364 1511 is-4 ta-365 sp-4 an-365 1512 is-4 ta-366 sp-4 an-366 1513 is-4 ta-367 sp-4 an-367 1514 is-4 ta-368 sp-4 an-368 1515 is-4 ta-369 sp-4 an-369 1516 is-4 ta-370 sp-4 an-370 1517 is-4 ta-371 sp-4 an-371 1518 is-4 ta-372 sp-4 an-372 1519 is-4 ta-373 sp-4 an-373 1520 is-4 ta-374 sp-4 an-374 1521 is-4 ta-375 sp-4 an-375 1522 is-4 ta-376 sp-4 an-376 1523 is-4 ta-377 sp-4 an-377 1524 is-5 ta-1 sp-5 an-1 1525 is-5 ta-2 sp-5 an-2 1526 is-5 ta-3 sp-5 an-3 1527 is-5 ta-4 sp-5 an-4 1528 is-5 ta-5 sp-5 an-5 1529 is-5 ta-6 sp-5 an-6 1530 is-5 ta-7 sp-5 an-7 1531 is-5 ta-8 sp-5 an-8 1532 is-5 ta-9 sp-5 an-9 1533 is-5 ta-10 sp-5 an-10 1534 is-5 ta-11 sp-5 an-11 1535 is-5 ta-12 sp-5 an-12 1536 is-5 ta-13 sp-5 an-13 1537 is-5 ta-14 sp-5 an-14 1538 is-5 ta-15 sp-5 an-15 1539 is-5 ta-16 sp-5 an-16 1540 is-5 ta-17 sp-5 an-17 1541 is-5 ta-18 sp-5 an-18 1542 is-5 ta-19 sp-5 an-19 1543 is-5 ta-20 sp-5 an-20 1544 is-5 ta-21 sp-5 an-21 1545 is-5 ta-22 sp-5 an-22 1546 is-5 ta-23 sp-5 an-23 1547 is-5 ta-24 sp-5 an-24 1548 is-5 ta-25 sp-5 an-25 1549 is-5 ta-26 sp-5 an-26 1550 is-5 ta-27 sp-5 an-27 1551 is-5 ta-28 sp-5 an-28 1552 is-5 ta-29 sp-5 an-29 1553 is-5 ta-30 sp-5 an-30 1554 is-5 ta-31 sp-5 an-31 1555 is-5 ta-32 sp-5 an-32 1556 is-5 ta-33 sp-5 an-33 1557 is-5 ta-34 sp-5 an-34 1558 is-5 ta-35 sp-5 an-35 1559 is-5 ta-36 sp-5 an-36 1560 is-5 ta-37 sp-5 an-37 1561 is-5 ta-38 sp-5 an-38 1562 is-5 ta-39 sp-5 an-39 1563 is-5 ta-40 sp-5 an-40 1564 is-5 ta-41 sp-5 an-41 1565 is-5 ta-42 sp-5 an-42 1566 is-5 ta-43 sp-5 an-43 1567 is-5 ta-44 sp-5 an-44 1568 is-5 ta-45 sp-5 an-45 1569 is-5 ta-46 sp-5 an-46 1570 is-5 ta-47 sp-5 an-47 1571 is-5 ta-48 sp-5 an-48 1572 is-5 ta-49 sp-5 an-49 1573 is-5 ta-50 sp-5 an-50 1574 is-5 ta-51 sp-5 an-51 1575 is-5 ta-52 sp-5 an-52 1576 is-5 ta-53 sp-5 an-53 1577 is-5 ta-54 sp-5 an-54 1578 is-5 ta-55 sp-5 an-55 1579 is-5 ta-56 sp-5 an-56 1580 is-5 ta-57 sp-5 an-57 1581 is-5 ta-58 sp-5 an-58 1582 is-5 ta-59 sp-5 an-59 1583 is-5 ta-60 sp-5 an-60 1584 is-5 ta-61 sp-5 an-61 1585 is-5 ta-62 sp-5 an-62 1586 is-5 ta-63 sp-5 an-63 1587 is-5 ta-64 sp-5 an-64 1588 is-5 ta-65 sp-5 an-65 1589 is-5 ta-66 sp-5 an-66 1590 is-5 ta-67 sp-5 an-67 1591 is-5 ta-68 sp-5 an-68 1592 is-5 ta-69 sp-5 an-69 1593 is-5 ta-70 sp-5 an-70 1594 is-5 ta-71 sp-5 an-71 1595 is-5 ta-72 sp-5 an-72 1596 is-5 ta-73 sp-5 an-73 1597 is-5 ta-74 sp-5 an-74 1598 is-5 ta-75 sp-5 an-75 1599 is-5 ta-76 sp-5 an-76 1600 is-5 ta-77 sp-5 an-77 1601 is-5 ta-78 sp-5 an-78 1602 is-5 ta-79 sp-5 an-79 1603 is-5 ta-80 sp-5 an-80 1604 is-5 ta-81 sp-5 an-81 1605 is-5 ta-82 sp-5 an-82 1606 is-5 ta-83 sp-5 an-83 1607 is-5 ta-84 sp-5 an-84 1608 is-5 ta-85 sp-5 an-85 1609 is-5 ta-86 sp-5 an-86 1610 is-5 ta-87 sp-5 an-87 1611 is-5 ta-88 sp-5 an-88 1612 is-5 ta-89 sp-5 an-89 1613 is-5 ta-90 sp-5 an-90 1614 is-5 ta-91 sp-5 an-91 1615 is-5 ta-92 sp-5 an-92 1616 is-5 ta-93 sp-5 an-93 1617 is-5 ta-94 sp-5 an-94 1618 is-5 ta-95 sp-5 an-95 1619 is-5 ta-96 sp-5 an-96 1620 is-5 ta-97 sp-5 an-97 1621 is-5 ta-98 sp-5 an-98 1622 is-5 ta-99 sp-5 an-99 1623 is-5 ta-100 sp-5 an-100 1624 is-5 ta-101 sp-5 an-101 1625 is-5 ta-102 sp-5 an-102 1626 is-5 ta-103 sp-5 an-103 1627 is-5 ta-104 sp-5 an-104 1628 is-5 ta-105 sp-5 an-105 1629 is-5 ta-106 sp-5 an-106 1630 is-5 ta-107 sp-5 an-107 1631 is-5 ta-108 sp-5 an-108 1632 is-5 ta-109 sp-5 an-109 1633 is-5 ta-110 sp-5 an-110 1634 is-5 ta-111 sp-5 an-111 1635 is-5 ta-112 sp-5 an-112 1636 is-5 ta-113 sp-5 an-113 1637 is-5 ta-114 sp-5 an-114 1638 is-5 ta-115 sp-5 an-115 1639 is-5 ta-116 sp-5 an-116 1640 is-5 ta-117 sp-5 an-117 1641 is-5 ta-118 sp-5 an-118 1642 is-5 ta-119 sp-5 an-119 1643 is-5 ta-120 sp-5 an-120 1644 is-5 ta-121 sp-5 an-121 1645 is-5 ta-122 sp-5 an-122 1646 is-5 ta-123 sp-5 an-123 1647 is-5 ta-124 sp-5 an-124 1648 is-5 ta-125 sp-5 an-125 1649 is-5 ta-126 sp-5 an-126 1650 is-5 ta-127 sp-5 an-127 1651 is-5 ta-128 sp-5 an-128 1652 is-5 ta-129 sp-5 an-129 1653 is-5 ta-130 sp-5 an-130 1654 is-5 ta-131 sp-5 an-131 1655 is-5 ta-132 sp-5 an-132 1656 is-5 ta-133 sp-5 an-133 1657 is-5 ta-134 sp-5 an-134 1658 is-5 ta-135 sp-5 an-135 1659 is-5 ta-136 sp-5 an-136 1660 is-5 ta-137 sp-5 an-137 1661 is-5 ta-138 sp-5 an-138 1662 is-5 ta-139 sp-5 an-139 1663 is-5 ta-140 sp-5 an-140 1664 is-5 ta-141 sp-5 an-141 1665 is-5 ta-142 sp-5 an-142 1666 is-5 ta-143 sp-5 an-143 1667 is-5 ta-144 sp-5 an-144 1668 is-5 ta-145 sp-5 an-145 1669 is-5 ta-146 sp-5 an-146 1670 is-5 ta-147 sp-5 an-147 1671 is-5 ta-148 sp-5 an-148 1672 is-5 ta-149 sp-5 an-149 1673 is-5 ta-150 sp-5 an-150 1674 is-5 ta-151 sp-5 an-151 1675 is-5 ta-152 sp-5 an-152 1676 is-5 ta-153 sp-5 an-153 1677 is-5 ta-154 sp-5 an-154 1678 is-5 ta-155 sp-5 an-155 1679 is-5 ta-156 sp-5 an-156 1680 is-5 ta-157 sp-5 an-157 1681 is-5 ta-158 sp-5 an-158 1682 is-5 ta-159 sp-5 an-159 1683 is-5 ta-160 sp-5 an-160 1684 is-5 ta-161 sp-5 an-161 1685 is-5 ta-162 sp-5 an-162 1686 is-5 ta-163 sp-5 an-163 1687 is-5 ta-164 sp-5 an-164 1688 is-5 ta-165 sp-5 an-165 1689 is-5 ta-166 sp-5 an-166 1690 is-5 ta-167 sp-5 an-167 1691 is-5 ta-168 sp-5 an-168 1692 is-5 ta-169 sp-5 an-169 1693 is-5 ta-170 sp-5 an-170 1694 is-5 ta-171 sp-5 an-171 1695 is-5 ta-172 sp-5 an-172 1696 is-5 ta-173 sp-5 an-173 1697 is-5 ta-174 sp-5 an-174 1698 is-5 ta-175 sp-5 an-175 1699 is-5 ta-176 sp-5 an-176 1700 is-5 ta-177 sp-5 an-177 1701 is-5 ta-178 sp-5 an-178 1702 is-5 ta-179 sp-5 an-179 1703 is-5 ta-180 sp-5 an-180 1704 is-5 ta-181 sp-5 an-181 1705 is-5 ta-182 sp-5 an-182 1706 is-5 ta-183 sp-5 an-183 1707 is-5 ta-184 sp-5 an-184 1708 is-5 ta-185 sp-5 an-185 1709 is-5 ta-186 sp-5 an-186 1710 is-5 ta-187 sp-5 an-187 1711 is-5 ta-188 sp-5 an-188 1712 is-5 ta-189 sp-5 an-189 1713 is-5 ta-190 sp-5 an-190 1714 is-5 ta-191 sp-5 an-191 1715 is-5 ta-192 sp-5 an-192 1716 is-5 ta-193 sp-5 an-193 1717 is-5 ta-194 sp-5 an-194 1718 is-5 ta-195 sp-5 an-195 1719 is-5 ta-196 sp-5 an-196 1720 is-5 ta-197 sp-5 an-197 1721 is-5 ta-198 sp-5 an-198 1722 is-5 ta-199 sp-5 an-199 1723 is-5 ta-200 sp-5 an-200 1724 is-5 ta-201 sp-5 an-201 1725 is-5 ta-202 sp-5 an-202 1726 is-5 ta-203 sp-5 an-203 1727 is-5 ta-204 sp-5 an-204 1728 is-5 ta-205 sp-5 an-205 1729 is-5 ta-206 sp-5 an-206 1730 is-5 ta-207 sp-5 an-207 1731 is-5 ta-208 sp-5 an-208 1732 is-5 ta-209 sp-5 an-209 1733 is-5 ta-210 sp-5 an-210 1734 is-5 ta-211 sp-5 an-211 1735 is-5 ta-212 sp-5 an-212 1736 is-5 ta-213 sp-5 an-213 1737 is-5 ta-214 sp-5 an-214 1738 is-5 ta-215 sp-5 an-215 1739 is-5 ta-216 sp-5 an-216 1740 is-5 ta-217 sp-5 an-217 1741 is-5 ta-218 sp-5 an-218 1742 is-5 ta-219 sp-5 an-219 1743 is-5 ta-220 sp-5 an-220 1744 is-5 ta-221 sp-5 an-221 1745 is-5 ta-222 sp-5 an-222 1746 is-5 ta-223 sp-5 an-223 1747 is-5 ta-224 sp-5 an-224 1748 is-5 ta-225 sp-5 an-225 1749 is-5 ta-226 sp-5 an-226 1750 is-5 ta-227 sp-5 an-227 1751 is-5 ta-228 sp-5 an-228 1752 is-5 ta-229 sp-5 an-229 1753 is-5 ta-230 sp-5 an-230 1754 is-5 ta-231 sp-5 an-231 1755 is-5 ta-232 sp-5 an-232 1756 is-5 ta-233 sp-5 an-233 1757 is-5 ta-234 sp-5 an-234 1758 is-5 ta-235 sp-5 an-235 1759 is-5 ta-236 sp-5 an-236 1760 is-5 ta-237 sp-5 an-237 1761 is-5 ta-238 sp-5 an-238 1762 is-5 ta-239 sp-5 an-239 1763 is-5 ta-240 sp-5 an-240 1764 is-5 ta-241 sp-5 an-241 1765 is-5 ta-242 sp-5 an-242 1766 is-5 ta-243 sp-5 an-243 1767 is-5 ta-244 sp-5 an-244 1768 is-5 ta-245 sp-5 an-245 1769 is-5 ta-246 sp-5 an-246 1770 is-5 ta-247 sp-5 an-247 1771 is-5 ta-248 sp-5 an-248 1772 is-5 ta-249 sp-5 an-249 1773 is-5 ta-250 sp-5 an-250 1774 is-5 ta-251 sp-5 an-251 1775 is-5 ta-252 sp-5 an-252 1776 is-5 ta-253 sp-5 an-253 1777 is-5 ta-254 sp-5 an-254 1778 is-5 ta-255 sp-5 an-255 1779 is-5 ta-256 sp-5 an-256 1780 is-5 ta-257 sp-5 an-257 1781 is-5 ta-258 sp-5 an-258 1782 is-5 ta-259 sp-5 an-259 1783 is-5 ta-260 sp-5 an-260 1784 is-5 ta-261 sp-5 an-261 1785 is-5 ta-262 sp-5 an-262 1786 is-5 ta-263 sp-5 an-263 1787 is-5 ta-264 sp-5 an-264 1788 is-5 ta-265 sp-5 an-265 1789 is-5 ta-266 sp-5 an-266 1790 is-5 ta-267 sp-5 an-267 1791 is-5 ta-268 sp-5 an-268 1792 is-5 ta-269 sp-5 an-269 1793 is-5 ta-270 sp-5 an-270 1794 is-5 ta-271 sp-5 an-271 1795 is-5 ta-272 sp-5 an-272 1796 is-5 ta-273 sp-5 an-273 1797 is-5 ta-274 sp-5 an-274 1798 is-5 ta-275 sp-5 an-275 1799 is-5 ta-276 sp-5 an-276 1800 is-5 ta-277 sp-5 an-277 1801 is-5 ta-278 sp-5 an-278 1802 is-5 ta-279 sp-5 an-279 1803 is-5 ta-280 sp-5 an-280 1804 is-5 ta-281 sp-5 an-281 1805 is-5 ta-282 sp-5 an-282 1806 is-5 ta-283 sp-5 an-283 1807 is-5 ta-284 sp-5 an-284 1808 is-5 ta-285 sp-5 an-285 1809 is-5 ta-286 sp-5 an-286 1810 is-5 ta-287 sp-5 an-287 1811 is-5 ta-288 sp-5 an-288 1812 is-5 ta-289 sp-5 an-289 1813 is-5 ta-290 sp-5 an-290 1814 is-5 ta-291 sp-5 an-291 1815 is-5 ta-292 sp-5 an-292 1816 is-5 ta-293 sp-5 an-293 1817 is-5 ta-294 sp-5 an-294 1818 is-5 ta-295 sp-5 an-295 1819 is-5 ta-296 sp-5 an-296 1820 is-5 ta-297 sp-5 an-297 1821 is-5 ta-298 sp-5 an-298 1822 is-5 ta-299 sp-5 an-299 1823 is-5 ta-300 sp-5 an-300 1824 is-5 ta-301 sp-5 an-301 1825 is-5 ta-302 sp-5 an-302 1826 is-5 ta-303 sp-5 an-303 1827 is-5 ta-304 sp-5 an-304 1828 is-5 ta-305 sp-5 an-305 1829 is-5 ta-306 sp-5 an-306 1830 is-5 ta-307 sp-5 an-307 1831 is-5 ta-308 sp-5 an-308 1832 is-5 ta-309 sp-5 an-309 1833 is-5 ta-310 sp-5 an-310 1834 is-5 ta-311 sp-5 an-311 1835 is-5 ta-312 sp-5 an-312 1836 is-5 ta-313 sp-5 an-313 1837 is-5 ta-314 sp-5 an-314 1838 is-5 ta-315 sp-5 an-315 1839 is-5 ta-316 sp-5 an-316 1840 is-5 ta-317 sp-5 an-317 1841 is-5 ta-318 sp-5 an-318 1842 is-5 ta-319 sp-5 an-319 1843 is-5 ta-320 sp-5 an-320 1844 is-5 ta-321 sp-5 an-321 1845 is-5 ta-322 sp-5 an-322 1846 is-5 ta-323 sp-5 an-323 1847 is-5 ta-324 sp-5 an-324 1848 is-5 ta-325 sp-5 an-325 1849 is-5 ta-326 sp-5 an-326 1850 is-5 ta-327 sp-5 an-327 1851 is-5 ta-328 sp-5 an-328 1852 is-5 ta-329 sp-5 an-329 1853 is-5 ta-330 sp-5 an-330 1854 is-5 ta-331 sp-5 an-331 1855 is-5 ta-332 sp-5 an-332 1856 is-5 ta-333 sp-5 an-333 1857 is-5 ta-334 sp-5 an-334 1858 is-5 ta-335 sp-5 an-335 1859 is-5 ta-336 sp-5 an-336 1860 is-5 ta-337 sp-5 an-337 1861 is-5 ta-338 sp-5 an-338 1862 is-5 ta-339 sp-5 an-339 1863 is-5 ta-340 sp-5 an-340 1864 is-5 ta-341 sp-5 an-341 1865 is-5 ta-342 sp-5 an-342 1866 is-5 ta-343 sp-5 an-343 1867 is-5 ta-344 sp-5 an-344 1868 is-5 ta-345 sp-5 an-345 1869 is-5 ta-346 sp-5 an-346 1870 is-5 ta-347 sp-5 an-347 1871 is-5 ta-348 sp-5 an-348 1872 is-5 ta-349 sp-5 an-349 1873 is-5 ta-350 sp-5 an-350 1874 is-5 ta-351 sp-5 an-351 1875 is-5 ta-352 sp-5 an-352 1876 is-5 ta-353 sp-5 an-353 1877 is-5 ta-354 sp-5 an-354 1878 is-5 ta-355 sp-5 an-355 1879 is-5 ta-356 sp-5 an-356 1880 is-5 ta-357 sp-5 an-357 1881 is-5 ta-358 sp-5 an-358 1882 is-5 ta-359 sp-5 an-359 1883 is-5 ta-360 sp-5 an-360 1884 is-5 ta-361 sp-5 an-361 1885 is-5 ta-362 sp-5 an-362 1886 is-5 ta-363 sp-5 an-363 1887 is-5 ta-364 sp-5 an-364 1888 is-5 ta-365 sp-5 an-365 1889 is-5 ta-366 sp-5 an-366 1890 is-5 ta-367 sp-5 an-367 1891 is-5 ta-368 sp-5 an-368 1892 is-5 ta-369 sp-5 an-369 1893 is-5 ta-370 sp-5 an-370 1894 is-5 ta-371 sp-5 an-371 1895 is-5 ta-372 sp-5 an-372 1896 is-5 ta-373 sp-5 an-373 1897 is-5 ta-374 sp-5 an-374 1898 is-5 ta-375 sp-5 an-375 1899 is-5 ta-376 sp-5 an-376 1900 is-5 ta-377 sp-5 an-377 1901 is-6 ta-1 sp-6 an-1 1902 is-6 ta-2 sp-6 an-2 1903 is-6 ta-3 sp-6 an-3 1904 is-6 ta-4 sp-6 an-4 1905 is-6 ta-5 sp-6 an-5 1906 is-6 ta-6 sp-6 an-6 1907 is-6 ta-7 sp-6 an-7 1908 is-6 ta-8 sp-6 an-8 1909 is-6 ta-9 sp-6 an-9 1910 is-6 ta-10 sp-6 an-10 1911 is-6 ta-11 sp-6 an-11 1912 is-6 ta-12 sp-6 an-12 1913 is-6 ta-13 sp-6 an-13 1914 is-6 ta-14 sp-6 an-14 1915 is-6 ta-15 sp-6 an-15 1916 is-6 ta-16 sp-6 an-16 1917 is-6 ta-17 sp-6 an-17 1918 is-6 ta-18 sp-6 an-18 1919 is-6 ta-19 sp-6 an-19 1920 is-6 ta-20 sp-6 an-20 1921 is-6 ta-21 sp-6 an-21 1922 is-6 ta-22 sp-6 an-22 1923 is-6 ta-23 sp-6 an-23 1924 is-6 ta-24 sp-6 an-24 1925 is-6 ta-25 sp-6 an-25 1926 is-6 ta-26 sp-6 an-26 1927 is-6 ta-27 sp-6 an-27 1928 is-6 ta-28 sp-6 an-28 1929 is-6 ta-29 sp-6 an-29 1930 is-6 ta-30 sp-6 an-30 1931 is-6 ta-31 sp-6 an-31 1932 is-6 ta-32 sp-6 an-32 1933 is-6 ta-33 sp-6 an-33 1934 is-6 ta-34 sp-6 an-34 1935 is-6 ta-35 sp-6 an-35 1936 is-6 ta-36 sp-6 an-36 1937 is-6 ta-37 sp-6 an-37 1938 is-6 ta-38 sp-6 an-38 1939 is-6 ta-39 sp-6 an-39 1940 is-6 ta-40 sp-6 an-40 1941 is-6 ta-41 sp-6 an-41 1942 is-6 ta-42 sp-6 an-42 1943 is-6 ta-43 sp-6 an-43 1944 is-6 ta-44 sp-6 an-44 1945 is-6 ta-45 sp-6 an-45 1946 is-6 ta-46 sp-6 an-46 1947 is-6 ta-47 sp-6 an-47 1948 is-6 ta-48 sp-6 an-48 1949 is-6 ta-49 sp-6 an-49 1950 is-6 ta-50 sp-6 an-50 1951 is-6 ta-51 sp-6 an-51 1952 is-6 ta-52 sp-6 an-52 1953 is-6 ta-53 sp-6 an-53 1954 is-6 ta-54 sp-6 an-54 1955 is-6 ta-55 sp-6 an-55 1956 is-6 ta-56 sp-6 an-56 1957 is-6 ta-57 sp-6 an-57 1958 is-6 ta-58 sp-6 an-58 1959 is-6 ta-59 sp-6 an-59 1960 is-6 ta-60 sp-6 an-60 1961 is-6 ta-61 sp-6 an-61 1962 is-6 ta-62 sp-6 an-62 1963 is-6 ta-63 sp-6 an-63 1964 is-6 ta-64 sp-6 an-64 1965 is-6 ta-65 sp-6 an-65 1966 is-6 ta-66 sp-6 an-66 1967 is-6 ta-67 sp-6 an-67 1968 is-6 ta-68 sp-6 an-68 1969 is-6 ta-69 sp-6 an-69 1970 is-6 ta-70 sp-6 an-70 1971 is-6 ta-71 sp-6 an-71 1972 is-6 ta-72 sp-6 an-72 1973 is-6 ta-73 sp-6 an-73 1974 is-6 ta-74 sp-6 an-74 1975 is-6 ta-75 sp-6 an-75 1976 is-6 ta-76 sp-6 an-76 1977 is-6 ta-77 sp-6 an-77 1978 is-6 ta-78 sp-6 an-78 1979 is-6 ta-79 sp-6 an-79 1980 is-6 ta-80 sp-6 an-80 1981 is-6 ta-81 sp-6 an-81 1982 is-6 ta-82 sp-6 an-82 1983 is-6 ta-83 sp-6 an-83 1984 is-6 ta-84 sp-6 an-84 1985 is-6 ta-85 sp-6 an-85 1986 is-6 ta-86 sp-6 an-86 1987 is-6 ta-87 sp-6 an-87 1988 is-6 ta-88 sp-6 an-88 1989 is-6 ta-89 sp-6 an-89 1990 is-6 ta-90 sp-6 an-90 1991 is-6 ta-91 sp-6 an-91 1992 is-6 ta-92 sp-6 an-92 1993 is-6 ta-93 sp-6 an-93 1994 is-6 ta-94 sp-6 an-94 1995 is-6 ta-95 sp-6 an-95 1996 is-6 ta-96 sp-6 an-96 1997 is-6 ta-97 sp-6 an-97 1998 is-6 ta-98 sp-6 an-98 1999 is-6 ta-99 sp-6 an-99 2000 is-6 ta-100 sp-6 an-100 2001 is-6 ta-101 sp-6 an-101 2002 is-6 ta-102 sp-6 an-102 2003 is-6 ta-103 sp-6 an-103 2004 is-6 ta-104 sp-6 an-104 2005 is-6 ta-105 sp-6 an-105 2006 is-6 ta-106 sp-6 an-106 2007 is-6 ta-107 sp-6 an-107 2008 is-6 ta-108 sp-6 an-108 2009 is-6 ta-109 sp-6 an-109 2010 is-6 ta-110 sp-6 an-110 2011 is-6 ta-111 sp-6 an-111 2012 is-6 ta-112 sp-6 an-112 2013 is-6 ta-113 sp-6 an-113 2014 is-6 ta-114 sp-6 an-114 2015 is-6 ta-115 sp-6 an-115 2016 is-6 ta-116 sp-6 an-116 2017 is-6 ta-117 sp-6 an-117 2018 is-6 ta-118 sp-6 an-118 2019 is-6 ta-119 sp-6 an-119 2020 is-6 ta-120 sp-6 an-120 2021 is-6 ta-121 sp-6 an-121 2022 is-6 ta-122 sp-6 an-122 2023 is-6 ta-123 sp-6 an-123 2024 is-6 ta-124 sp-6 an-124 2025 is-6 ta-125 sp-6 an-125 2026 is-6 ta-126 sp-6 an-126 2027 is-6 ta-127 sp-6 an-127 2028 is-6 ta-128 sp-6 an-128 2029 is-6 ta-129 sp-6 an-129 2030 is-6 ta-130 sp-6 an-130 2031 is-6 ta-131 sp-6 an-131 2032 is-6 ta-132 sp-6 an-132 2033 is-6 ta-133 sp-6 an-133 2034 is-6 ta-134 sp-6 an-134 2035 is-6 ta-135 sp-6 an-135 2036 is-6 ta-136 sp-6 an-136 2037 is-6 ta-137 sp-6 an-137 2038 is-6 ta-138 sp-6 an-138 2039 is-6 ta-139 sp-6 an-139 2040 is-6 ta-140 sp-6 an-140 2041 is-6 ta-141 sp-6 an-141 2042 is-6 ta-142 sp-6 an-142 2043 is-6 ta-143 sp-6 an-143 2044 is-6 ta-144 sp-6 an-144 2045 is-6 ta-145 sp-6 an-145 2046 is-6 ta-146 sp-6 an-146 2047 is-6 ta-147 sp-6 an-147 2048 is-6 ta-148 sp-6 an-148 2049 is-6 ta-149 sp-6 an-149 2050 is-6 ta-150 sp-6 an-150 2051 is-6 ta-151 sp-6 an-151 2052 is-6 ta-152 sp-6 an-152 2053 is-6 ta-153 sp-6 an-153 2054 is-6 ta-154 sp-6 an-154 2055 is-6 ta-155 sp-6 an-155 2056 is-6 ta-156 sp-6 an-156 2057 is-6 ta-157 sp-6 an-157 2058 is-6 ta-158 sp-6 an-158 2059 is-6 ta-159 sp-6 an-159 2060 is-6 ta-160 sp-6 an-160 2061 is-6 ta-161 sp-6 an-161 2062 is-6 ta-162 sp-6 an-162 2063 is-6 ta-163 sp-6 an-163 2064 is-6 ta-164 sp-6 an-164 2065 is-6 ta-165 sp-6 an-165 2066 is-6 ta-166 sp-6 an-166 2067 is-6 ta-167 sp-6 an-167 2068 is-6 ta-168 sp-6 an-168 2069 is-6 ta-169 sp-6 an-169 2070 is-6 ta-170 sp-6 an-170 2071 is-6 ta-171 sp-6 an-171 2072 is-6 ta-172 sp-6 an-172 2073 is-6 ta-173 sp-6 an-173 2074 is-6 ta-174 sp-6 an-174 2075 is-6 ta-175 sp-6 an-175 2076 is-6 ta-176 sp-6 an-176 2077 is-6 ta-177 sp-6 an-177 2078 is-6 ta-178 sp-6 an-178 2079 is-6 ta-179 sp-6 an-179 2080 is-6 ta-180 sp-6 an-180 2081 is-6 ta-181 sp-6 an-181 2082 is-6 ta-182 sp-6 an-182 2083 is-6 ta-183 sp-6 an-183 2084 is-6 ta-184 sp-6 an-184 2085 is-6 ta-185 sp-6 an-185 2086 is-6 ta-186 sp-6 an-186 2087 is-6 ta-187 sp-6 an-187 2088 is-6 ta-188 sp-6 an-188 2089 is-6 ta-189 sp-6 an-189 2090 is-6 ta-190 sp-6 an-190 2091 is-6 ta-191 sp-6 an-191 2092 is-6 ta-192 sp-6 an-192 2093 is-6 ta-193 sp-6 an-193 2094 is-6 ta-194 sp-6 an-194 2095 is-6 ta-195 sp-6 an-195 2096 is-6 ta-196 sp-6 an-196 2097 is-6 ta-197 sp-6 an-197 2098 is-6 ta-198 sp-6 an-198 2099 is-6 ta-199 sp-6 an-199 2100 is-6 ta-200 sp-6 an-200 2101 is-6 ta-201 sp-6 an-201 2102 is-6 ta-202 sp-6 an-202 2103 is-6 ta-203 sp-6 an-203 2104 is-6 ta-204 sp-6 an-204 2105 is-6 ta-205 sp-6 an-205 2106 is-6 ta-206 sp-6 an-206 2107 is-6 ta-207 sp-6 an-207 2108 is-6 ta-208 sp-6 an-208 2109 is-6 ta-209 sp-6 an-209 2110 is-6 ta-210 sp-6 an-210 2111 is-6 ta-211 sp-6 an-211 2112 is-6 ta-212 sp-6 an-212 2113 is-6 ta-213 sp-6 an-213 2114 is-6 ta-214 sp-6 an-214 2115 is-6 ta-215 sp-6 an-215 2116 is-6 ta-216 sp-6 an-216 2117 is-6 ta-217 sp-6 an-217 2118 is-6 ta-218 sp-6 an-218 2119 is-6 ta-219 sp-6 an-219 2120 is-6 ta-220 sp-6 an-220 2121 is-6 ta-221 sp-6 an-221 2122 is-6 ta-222 sp-6 an-222 2123 is-6 ta-223 sp-6 an-223 2124 is-6 ta-224 sp-6 an-224 2125 is-6 ta-225 sp-6 an-225 2126 is-6 ta-226 sp-6 an-226 2127 is-6 ta-227 sp-6 an-227 2128 is-6 ta-228 sp-6 an-228 2129 is-6 ta-229 sp-6 an-229 2130 is-6 ta-230 sp-6 an-230 2131 is-6 ta-231 sp-6 an-231 2132 is-6 ta-232 sp-6 an-232 2133 is-6 ta-233 sp-6 an-233 2134 is-6 ta-234 sp-6 an-234 2135 is-6 ta-235 sp-6 an-235 2136 is-6 ta-236 sp-6 an-236 2137 is-6 ta-237 sp-6 an-237 2138 is-6 ta-238 sp-6 an-238 2139 is-6 ta-239 sp-6 an-239 2140 is-6 ta-240 sp-6 an-240 2141 is-6 ta-241 sp-6 an-241 2142 is-6 ta-242 sp-6 an-242 2143 is-6 ta-243 sp-6 an-243 2144 is-6 ta-244 sp-6 an-244 2145 is-6 ta-245 sp-6 an-245 2146 is-6 ta-246 sp-6 an-246 2147 is-6 ta-247 sp-6 an-247 2148 is-6 ta-248 sp-6 an-248 2149 is-6 ta-249 sp-6 an-249 2150 is-6 ta-250 sp-6 an-250 2151 is-6 ta-251 sp-6 an-251 2152 is-6 ta-252 sp-6 an-252 2153 is-6 ta-253 sp-6 an-253 2154 is-6 ta-254 sp-6 an-254 2155 is-6 ta-255 sp-6 an-255 2156 is-6 ta-256 sp-6 an-256 2157 is-6 ta-257 sp-6 an-257 2158 is-6 ta-258 sp-6 an-258 2159 is-6 ta-259 sp-6 an-259 2160 is-6 ta-260 sp-6 an-260 2161 is-6 ta-261 sp-6 an-261 2162 is-6 ta-262 sp-6 an-262 2163 is-6 ta-263 sp-6 an-263 2164 is-6 ta-264 sp-6 an-264 2165 is-6 ta-265 sp-6 an-265 2166 is-6 ta-266 sp-6 an-266 2167 is-6 ta-267 sp-6 an-267 2168 is-6 ta-268 sp-6 an-268 2169 is-6 ta-269 sp-6 an-269 2170 is-6 ta-270 sp-6 an-270 2171 is-6 ta-271 sp-6 an-271 2172 is-6 ta-272 sp-6 an-272 2173 is-6 ta-273 sp-6 an-273 2174 is-6 ta-274 sp-6 an-274 2175 is-6 ta-275 sp-6 an-275 2176 is-6 ta-276 sp-6 an-276 2177 is-6 ta-277 sp-6 an-277 2178 is-6 ta-278 sp-6 an-278 2179 is-6 ta-279 sp-6 an-279 2180 is-6 ta-280 sp-6 an-280 2181 is-6 ta-281 sp-6 an-281 2182 is-6 ta-282 sp-6 an-282 2183 is-6 ta-283 sp-6 an-283 2184 is-6 ta-284 sp-6 an-284 2185 is-6 ta-285 sp-6 an-285 2186 is-6 ta-286 sp-6 an-286 2187 is-6 ta-287 sp-6 an-287 2188 is-6 ta-288 sp-6 an-288 2189 is-6 ta-289 sp-6 an-289 2190 is-6 ta-290 sp-6 an-290 2191 is-6 ta-291 sp-6 an-291 2192 is-6 ta-292 sp-6 an-292 2193 is-6 ta-293 sp-6 an-293 2194 is-6 ta-294 sp-6 an-294 2195 is-6 ta-295 sp-6 an-295 2196 is-6 ta-296 sp-6 an-296 2197 is-6 ta-297 sp-6 an-297 2198 is-6 ta-298 sp-6 an-298 2199 is-6 ta-299 sp-6 an-299 2200 is-6 ta-300 sp-6 an-300 2201 is-6 ta-301 sp-6 an-301 2202 is-6 ta-302 sp-6 an-302 2203 is-6 ta-303 sp-6 an-303 2204 is-6 ta-304 sp-6 an-304 2205 is-6 ta-305 sp-6 an-305 2206 is-6 ta-306 sp-6 an-306 2207 is-6 ta-307 sp-6 an-307 2208 is-6 ta-308 sp-6 an-308 2209 is-6 ta-309 sp-6 an-309 2210 is-6 ta-310 sp-6 an-310 2211 is-6 ta-311 sp-6 an-311 2212 is-6 ta-312 sp-6 an-312 2213 is-6 ta-313 sp-6 an-313 2214 is-6 ta-314 sp-6 an-314 2215 is-6 ta-315 sp-6 an-315 2216 is-6 ta-316 sp-6 an-316 2217 is-6 ta-317 sp-6 an-317 2218 is-6 ta-318 sp-6 an-318 2219 is-6 ta-319 sp-6 an-319 2220 is-6 ta-320 sp-6 an-320 2221 is-6 ta-321 sp-6 an-321 2222 is-6 ta-322 sp-6 an-322 2223 is-6 ta-323 sp-6 an-323 2224 is-6 ta-324 sp-6 an-324 2225 is-6 ta-325 sp-6 an-325 2226 is-6 ta-326 sp-6 an-326 2227 is-6 ta-327 sp-6 an-327 2228 is-6 ta-328 sp-6 an-328 2229 is-6 ta-329 sp-6 an-329 2230 is-6 ta-330 sp-6 an-330 2231 is-6 ta-331 sp-6 an-331 2232 is-6 ta-332 sp-6 an-332 2233 is-6 ta-333 sp-6 an-333 2234 is-6 ta-334 sp-6 an-334 2235 is-6 ta-335 sp-6 an-335 2236 is-6 ta-336 sp-6 an-336 2237 is-6 ta-337 sp-6 an-337 2238 is-6 ta-338 sp-6 an-338 2239 is-6 ta-339 sp-6 an-339 2240 is-6 ta-340 sp-6 an-340 2241 is-6 ta-341 sp-6 an-341 2242 is-6 ta-342 sp-6 an-342 2243 is-6 ta-343 sp-6 an-343 2244 is-6 ta-344 sp-6 an-344 2245 is-6 ta-345 sp-6 an-345 2246 is-6 ta-346 sp-6 an-346 2247 is-6 ta-347 sp-6 an-347 2248 is-6 ta-348 sp-6 an-348 2249 is-6 ta-349 sp-6 an-349 2250 is-6 ta-350 sp-6 an-350 2251 is-6 ta-351 sp-6 an-351 2252 is-6 ta-352 sp-6 an-352 2253 is-6 ta-353 sp-6 an-353 2254 is-6 ta-354 sp-6 an-354 2255 is-6 ta-355 sp-6 an-355 2256 is-6 ta-356 sp-6 an-356 2257 is-6 ta-357 sp-6 an-357 2258 is-6 ta-358 sp-6 an-358 2259 is-6 ta-359 sp-6 an-359 2260 is-6 ta-360 sp-6 an-360 2261 is-6 ta-361 sp-6 an-361 2262 is-6 ta-362 sp-6 an-362 2263 is-6 ta-363 sp-6 an-363 2264 is-6 ta-364 sp-6 an-364 2265 is-6 ta-365 sp-6 an-365 2266 is-6 ta-366 sp-6 an-366 2267 is-6 ta-367 sp-6 an-367 2268 is-6 ta-368 sp-6 an-368 2269 is-6 ta-369 sp-6 an-369 2270 is-6 ta-370 sp-6 an-370 2271 is-6 ta-371 sp-6 an-371 2272 is-6 ta-372 sp-6 an-372 2273 is-6 ta-373 sp-6 an-373 2274 is-6 ta-374 sp-6 an-374 2275 is-6 ta-375 sp-6 an-375 2276 is-6 ta-376 sp-6 an-376 2277 is-6 ta-377 sp-6 an-377 2278 is-7 ta-1 sp-7 an-1 2279 is-7 ta-2 sp-7 an-2 2280 is-7 ta-3 sp-7 an-3 2281 is-7 ta-4 sp-7 an-4 2282 is-7 ta-5 sp-7 an-5 2283 is-7 ta-6 sp-7 an-6 2284 is-7 ta-7 sp-7 an-7 2285 is-7 ta-8 sp-7 an-8 2286 is-7 ta-9 sp-7 an-9 2287 is-7 ta-10 sp-7 an-10 2288 is-7 ta-11 sp-7 an-11 2289 is-7 ta-12 sp-7 an-12 2290 is-7 ta-13 sp-7 an-13 2291 is-7 ta-14 sp-7 an-14 2292 is-7 ta-15 sp-7 an-15 2293 is-7 ta-16 sp-7 an-16 2294 is-7 ta-17 sp-7 an-17 2295 is-7 ta-18 sp-7 an-18 2296 is-7 ta-19 sp-7 an-19 2297 is-7 ta-20 sp-7 an-20 2298 is-7 ta-21 sp-7 an-21 2299 is-7 ta-22 sp-7 an-22 2300 is-7 ta-23 sp-7 an-23 2301 is-7 ta-24 sp-7 an-24 2302 is-7 ta-25 sp-7 an-25 2303 is-7 ta-26 sp-7 an-26 2304 is-7 ta-27 sp-7 an-27 2305 is-7 ta-28 sp-7 an-28 2306 is-7 ta-29 sp-7 an-29 2307 is-7 ta-30 sp-7 an-30 2308 is-7 ta-31 sp-7 an-31 2309 is-7 ta-32 sp-7 an-32 2310 is-7 ta-33 sp-7 an-33 2311 is-7 ta-34 sp-7 an-34 2312 is-7 ta-35 sp-7 an-35 2313 is-7 ta-36 sp-7 an-36 2314 is-7 ta-37 sp-7 an-37 2315 is-7 ta-38 sp-7 an-38 2316 is-7 ta-39 sp-7 an-39 2317 is-7 ta-40 sp-7 an-40 2318 is-7 ta-41 sp-7 an-41 2319 is-7 ta-42 sp-7 an-42 2320 is-7 ta-43 sp-7 an-43 2321 is-7 ta-44 sp-7 an-44 2322 is-7 ta-45 sp-7 an-45 2323 is-7 ta-46 sp-7 an-46 2324 is-7 ta-47 sp-7 an-47 2325 is-7 ta-48 sp-7 an-48 2326 is-7 ta-49 sp-7 an-49 2327 is-7 ta-50 sp-7 an-50 2328 is-7 ta-51 sp-7 an-51 2329 is-7 ta-52 sp-7 an-52 2330 is-7 ta-53 sp-7 an-53 2331 is-7 ta-54 sp-7 an-54 2332 is-7 ta-55 sp-7 an-55 2333 is-7 ta-56 sp-7 an-56 2334 is-7 ta-57 sp-7 an-57 2335 is-7 ta-58 sp-7 an-58 2336 is-7 ta-59 sp-7 an-59 2337 is-7 ta-60 sp-7 an-60 2338 is-7 ta-61 sp-7 an-61 2339 is-7 ta-62 sp-7 an-62 2340 is-7 ta-63 sp-7 an-63 2341 is-7 ta-64 sp-7 an-64 2342 is-7 ta-65 sp-7 an-65 2343 is-7 ta-66 sp-7 an-66 2344 is-7 ta-67 sp-7 an-67 2345 is-7 ta-68 sp-7 an-68 2346 is-7 ta-69 sp-7 an-69 2347 is-7 ta-70 sp-7 an-70 2348 is-7 ta-71 sp-7 an-71 2349 is-7 ta-72 sp-7 an-72 2350 is-7 ta-73 sp-7 an-73 2351 is-7 ta-74 sp-7 an-74 2352 is-7 ta-75 sp-7 an-75 2353 is-7 ta-76 sp-7 an-76 2354 is-7 ta-77 sp-7 an-77 2355 is-7 ta-78 sp-7 an-78 2356 is-7 ta-79 sp-7 an-79 2357 is-7 ta-80 sp-7 an-80 2358 is-7 ta-81 sp-7 an-81 2359 is-7 ta-82 sp-7 an-82 2360 is-7 ta-83 sp-7 an-83 2361 is-7 ta-84 sp-7 an-84 2362 is-7 ta-85 sp-7 an-85 2363 is-7 ta-86 sp-7 an-86 2364 is-7 ta-87 sp-7 an-87 2365 is-7 ta-88 sp-7 an-88 2366 is-7 ta-89 sp-7 an-89 2367 is-7 ta-90 sp-7 an-90 2368 is-7 ta-91 sp-7 an-91 2369 is-7 ta-92 sp-7 an-92 2370 is-7 ta-93 sp-7 an-93 2371 is-7 ta-94 sp-7 an-94 2372 is-7 ta-95 sp-7 an-95 2373 is-7 ta-96 sp-7 an-96 2374 is-7 ta-97 sp-7 an-97 2375 is-7 ta-98 sp-7 an-98 2376 is-7 ta-99 sp-7 an-99 2377 is-7 ta-100 sp-7 an-100 2378 is-7 ta-101 sp-7 an-101 2379 is-7 ta-102 sp-7 an-102 2380 is-7 ta-103 sp-7 an-103 2381 is-7 ta-104 sp-7 an-104 2382 is-7 ta-105 sp-7 an-105 2383 is-7 ta-106 sp-7 an-106 2384 is-7 ta-107 sp-7 an-107 2385 is-7 ta-108 sp-7 an-108 2386 is-7 ta-109 sp-7 an-109 2387 is-7 ta-110 sp-7 an-110 2388 is-7 ta-111 sp-7 an-111 2389 is-7 ta-112 sp-7 an-112 2390 is-7 ta-113 sp-7 an-113 2391 is-7 ta-114 sp-7 an-114 2392 is-7 ta-115 sp-7 an-115 2393 is-7 ta-116 sp-7 an-116 2394 is-7 ta-117 sp-7 an-117 2395 is-7 ta-118 sp-7 an-118 2396 is-7 ta-119 sp-7 an-119 2397 is-7 ta-120 sp-7 an-120 2398 is-7 ta-121 sp-7 an-121 2399 is-7 ta-122 sp-7 an-122 2400 is-7 ta-123 sp-7 an-123 2401 is-7 ta-124 sp-7 an-124 2402 is-7 ta-125 sp-7 an-125 2403 is-7 ta-126 sp-7 an-126 2404 is-7 ta-127 sp-7 an-127 2405 is-7 ta-128 sp-7 an-128 2406 is-7 ta-129 sp-7 an-129 2407 is-7 ta-130 sp-7 an-130 2408 is-7 ta-131 sp-7 an-131 2409 is-7 ta-132 sp-7 an-132 2410 is-7 ta-133 sp-7 an-133 2411 is-7 ta-134 sp-7 an-134 2412 is-7 ta-135 sp-7 an-135 2413 is-7 ta-136 sp-7 an-136 2414 is-7 ta-137 sp-7 an-137 2415 is-7 ta-138 sp-7 an-138 2416 is-7 ta-139 sp-7 an-139 2417 is-7 ta-140 sp-7 an-140 2418 is-7 ta-141 sp-7 an-141 2419 is-7 ta-142 sp-7 an-142 2420 is-7 ta-143 sp-7 an-143 2421 is-7 ta-144 sp-7 an-144 2422 is-7 ta-145 sp-7 an-145 2423 is-7 ta-146 sp-7 an-146 2424 is-7 ta-147 sp-7 an-147 2425 is-7 ta-148 sp-7 an-148 2426 is-7 ta-149 sp-7 an-149 2427 is-7 ta-150 sp-7 an-150 2428 is-7 ta-151 sp-7 an-151 2429 is-7 ta-152 sp-7 an-152 2430 is-7 ta-153 sp-7 an-153 2431 is-7 ta-154 sp-7 an-154 2432 is-7 ta-155 sp-7 an-155 2433 is-7 ta-156 sp-7 an-156 2434 is-7 ta-157 sp-7 an-157 2435 is-7 ta-158 sp-7 an-158 2436 is-7 ta-159 sp-7 an-159 2437 is-7 ta-160 sp-7 an-160 2438 is-7 ta-161 sp-7 an-161 2439 is-7 ta-162 sp-7 an-162 2440 is-7 ta-163 sp-7 an-163 2441 is-7 ta-164 sp-7 an-164 2442 is-7 ta-165 sp-7 an-165 2443 is-7 ta-166 sp-7 an-166 2444 is-7 ta-167 sp-7 an-167 2445 is-7 ta-168 sp-7 an-168 2446 is-7 ta-169 sp-7 an-169 2447 is-7 ta-170 sp-7 an-170 2448 is-7 ta-171 sp-7 an-171 2449 is-7 ta-172 sp-7 an-172 2450 is-7 ta-173 sp-7 an-173 2451 is-7 ta-174 sp-7 an-174 2452 is-7 ta-175 sp-7 an-175 2453 is-7 ta-176 sp-7 an-176 2454 is-7 ta-177 sp-7 an-177 2455 is-7 ta-178 sp-7 an-178 2456 is-7 ta-179 sp-7 an-179 2457 is-7 ta-180 sp-7 an-180 2458 is-7 ta-181 sp-7 an-181 2459 is-7 ta-182 sp-7 an-182 2460 is-7 ta-183 sp-7 an-183 2461 is-7 ta-184 sp-7 an-184 2462 is-7 ta-185 sp-7 an-185 2463 is-7 ta-186 sp-7 an-186 2464 is-7 ta-187 sp-7 an-187 2465 is-7 ta-188 sp-7 an-188 2466 is-7 ta-189 sp-7 an-189 2467 is-7 ta-190 sp-7 an-190 2468 is-7 ta-191 sp-7 an-191 2469 is-7 ta-192 sp-7 an-192 2470 is-7 ta-193 sp-7 an-193 2471 is-7 ta-194 sp-7 an-194 2472 is-7 ta-195 sp-7 an-195 2473 is-7 ta-196 sp-7 an-196 2474 is-7 ta-197 sp-7 an-197 2475 is-7 ta-198 sp-7 an-198 2476 is-7 ta-199 sp-7 an-199 2477 is-7 ta-200 sp-7 an-200 2478 is-7 ta-201 sp-7 an-201 2479 is-7 ta-202 sp-7 an-202 2480 is-7 ta-203 sp-7 an-203 2481 is-7 ta-204 sp-7 an-204 2482 is-7 ta-205 sp-7 an-205 2483 is-7 ta-206 sp-7 an-206 2484 is-7 ta-207 sp-7 an-207 2485 is-7 ta-208 sp-7 an-208 2486 is-7 ta-209 sp-7 an-209 2487 is-7 ta-210 sp-7 an-210 2488 is-7 ta-211 sp-7 an-211 2489 is-7 ta-212 sp-7 an-212 2490 is-7 ta-213 sp-7 an-213 2491 is-7 ta-214 sp-7 an-214 2492 is-7 ta-215 sp-7 an-215 2493 is-7 ta-216 sp-7 an-216 2494 is-7 ta-217 sp-7 an-217 2495 is-7 ta-218 sp-7 an-218 2496 is-7 ta-219 sp-7 an-219 2497 is-7 ta-220 sp-7 an-220 2498 is-7 ta-221 sp-7 an-221 2499 is-7 ta-222 sp-7 an-222 2500 is-7 ta-223 sp-7 an-223 2501 is-7 ta-224 sp-7 an-224 2502 is-7 ta-225 sp-7 an-225 2503 is-7 ta-226 sp-7 an-226 2504 is-7 ta-227 sp-7 an-227 2505 is-7 ta-228 sp-7 an-228 2506 is-7 ta-229 sp-7 an-229 2507 is-7 ta-230 sp-7 an-230 2508 is-7 ta-231 sp-7 an-231 2509 is-7 ta-232 sp-7 an-232 2510 is-7 ta-233 sp-7 an-233 2511 is-7 ta-234 sp-7 an-234 2512 is-7 ta-235 sp-7 an-235 2513 is-7 ta-236 sp-7 an-236 2514 is-7 ta-237 sp-7 an-237 2515 is-7 ta-238 sp-7 an-238 2516 is-7 ta-239 sp-7 an-239 2517 is-7 ta-240 sp-7 an-240 2518 is-7 ta-241 sp-7 an-241 2519 is-7 ta-242 sp-7 an-242 2520 is-7 ta-243 sp-7 an-243 2521 is-7 ta-244 sp-7 an-244 2522 is-7 ta-245 sp-7 an-245 2523 is-7 ta-246 sp-7 an-246 2524 is-7 ta-247 sp-7 an-247 2525 is-7 ta-248 sp-7 an-248 2526 is-7 ta-249 sp-7 an-249 2527 is-7 ta-250 sp-7 an-250 2528 is-7 ta-251 sp-7 an-251 2529 is-7 ta-252 sp-7 an-252 2530 is-7 ta-253 sp-7 an-253 2531 is-7 ta-254 sp-7 an-254 2532 is-7 ta-255 sp-7 an-255 2533 is-7 ta-256 sp-7 an-256 2534 is-7 ta-257 sp-7 an-257 2535 is-7 ta-258 sp-7 an-258 2536 is-7 ta-259 sp-7 an-259 2537 is-7 ta-260 sp-7 an-260 2538 is-7 ta-261 sp-7 an-261 2539 is-7 ta-262 sp-7 an-262 2540 is-7 ta-263 sp-7 an-263 2541 is-7 ta-264 sp-7 an-264 2542 is-7 ta-265 sp-7 an-265 2543 is-7 ta-266 sp-7 an-266 2544 is-7 ta-267 sp-7 an-267 2545 is-7 ta-268 sp-7 an-268 2546 is-7 ta-269 sp-7 an-269 2547 is-7 ta-270 sp-7 an-270 2548 is-7 ta-271 sp-7 an-271 2549 is-7 ta-272 sp-7 an-272 2550 is-7 ta-273 sp-7 an-273 2551 is-7 ta-274 sp-7 an-274 2552 is-7 ta-275 sp-7 an-275 2553 is-7 ta-276 sp-7 an-276 2554 is-7 ta-277 sp-7 an-277 2555 is-7 ta-278 sp-7 an-278 2556 is-7 ta-279 sp-7 an-279 2557 is-7 ta-280 sp-7 an-280 2558 is-7 ta-281 sp-7 an-281 2559 is-7 ta-282 sp-7 an-282 2560 is-7 ta-283 sp-7 an-283 2561 is-7 ta-284 sp-7 an-284 2562 is-7 ta-285 sp-7 an-285 2563 is-7 ta-286 sp-7 an-286 2564 is-7 ta-287 sp-7 an-287 2565 is-7 ta-288 sp-7 an-288 2566 is-7 ta-289 sp-7 an-289 2567 is-7 ta-290 sp-7 an-290 2568 is-7 ta-291 sp-7 an-291 2569 is-7 ta-292 sp-7 an-292 2570 is-7 ta-293 sp-7 an-293 2571 is-7 ta-294 sp-7 an-294 2572 is-7 ta-295 sp-7 an-295 2573 is-7 ta-296 sp-7 an-296 2574 is-7 ta-297 sp-7 an-297 2575 is-7 ta-298 sp-7 an-298 2576 is-7 ta-299 sp-7 an-299 2577 is-7 ta-300 sp-7 an-300 2578 is-7 ta-301 sp-7 an-301 2579 is-7 ta-302 sp-7 an-302 2580 is-7 ta-303 sp-7 an-303 2581 is-7 ta-304 sp-7 an-304 2582 is-7 ta-305 sp-7 an-305 2583 is-7 ta-306 sp-7 an-306 2584 is-7 ta-307 sp-7 an-307 2585 is-7 ta-308 sp-7 an-308 2586 is-7 ta-309 sp-7 an-309 2587 is-7 ta-310 sp-7 an-310 2588 is-7 ta-311 sp-7 an-311 2589 is-7 ta-312 sp-7 an-312 2590 is-7 ta-313 sp-7 an-313 2591 is-7 ta-314 sp-7 an-314 2592 is-7 ta-315 sp-7 an-315 2593 is-7 ta-316 sp-7 an-316 2594 is-7 ta-317 sp-7 an-317 2595 is-7 ta-318 sp-7 an-318 2596 is-7 ta-319 sp-7 an-319 2597 is-7 ta-320 sp-7 an-320 2598 is-7 ta-321 sp-7 an-321 2599 is-7 ta-322 sp-7 an-322 2600 is-7 ta-323 sp-7 an-323 2601 is-7 ta-324 sp-7 an-324 2602 is-7 ta-325 sp-7 an-325 2603 is-7 ta-326 sp-7 an-326 2604 is-7 ta-327 sp-7 an-327 2605 is-7 ta-328 sp-7 an-328 2606 is-7 ta-329 sp-7 an-329 2607 is-7 ta-330 sp-7 an-330 2608 is-7 ta-331 sp-7 an-331 2609 is-7 ta-332 sp-7 an-332 2610 is-7 ta-333 sp-7 an-333 2611 is-7 ta-334 sp-7 an-334 2612 is-7 ta-335 sp-7 an-335 2613 is-7 ta-336 sp-7 an-336 2614 is-7 ta-337 sp-7 an-337 2615 is-7 ta-338 sp-7 an-338 2616 is-7 ta-339 sp-7 an-339 2617 is-7 ta-340 sp-7 an-340 2618 is-7 ta-341 sp-7 an-341 2619 is-7 ta-342 sp-7 an-342 2620 is-7 ta-343 sp-7 an-343 2621 is-7 ta-344 sp-7 an-344 2622 is-7 ta-345 sp-7 an-345 2623 is-7 ta-346 sp-7 an-346 2624 is-7 ta-347 sp-7 an-347 2625 is-7 ta-348 sp-7 an-348 2626 is-7 ta-349 sp-7 an-349 2627 is-7 ta-350 sp-7 an-350 2628 is-7 ta-351 sp-7 an-351 2629 is-7 ta-352 sp-7 an-352 2630 is-7 ta-353 sp-7 an-353 2631 is-7 ta-354 sp-7 an-354 2632 is-7 ta-355 sp-7 an-355 2633 is-7 ta-356 sp-7 an-356 2634 is-7 ta-357 sp-7 an-357 2635 is-7 ta-358 sp-7 an-358 2636 is-7 ta-359 sp-7 an-359 2637 is-7 ta-360 sp-7 an-360 2638 is-7 ta-361 sp-7 an-361 2639 is-7 ta-362 sp-7 an-362 2640 is-7 ta-363 sp-7 an-363 2641 is-7 ta-364 sp-7 an-364 2642 is-7 ta-365 sp-7 an-365 2643 is-7 ta-366 sp-7 an-366 2644 is-7 ta-367 sp-7 an-367 2645 is-7 ta-368 sp-7 an-368 2646 is-7 ta-369 sp-7 an-369 2647 is-7 ta-370 sp-7 an-370 2648 is-7 ta-371 sp-7 an-371 2649 is-7 ta-372 sp-7 an-372 2650 is-7 ta-373 sp-7 an-373 2651 is-7 ta-374 sp-7 an-374 2652 is-7 ta-375 sp-7 an-375 2653 is-7 ta-376 sp-7 an-376 2654 is-7 ta-377 sp-7 an-377 2655 is-8 ta-1 sp-8 an-1 2656 is-8 ta-2 sp-8 an-2 2657 is-8 ta-3 sp-8 an-3 2658 is-8 ta-4 sp-8 an-4 2659 is-8 ta-5 sp-8 an-5 2660 is-8 ta-6 sp-8 an-6 2661 is-8 ta-7 sp-8 an-7 2662 is-8 ta-8 sp-8 an-8 2663 is-8 ta-9 sp-8 an-9 2664 is-8 ta-10 sp-8 an-10 2665 is-8 ta-11 sp-8 an-11 2666 is-8 ta-12 sp-8 an-12 2667 is-8 ta-13 sp-8 an-13 2668 is-8 ta-14 sp-8 an-14 2669 is-8 ta-15 sp-8 an-15 2670 is-8 ta-16 sp-8 an-16 2671 is-8 ta-17 sp-8 an-17 2672 is-8 ta-18 sp-8 an-18 2673 is-8 ta-19 sp-8 an-19 2674 is-8 ta-20 sp-8 an-20 2675 is-8 ta-21 sp-8 an-21 2676 is-8 ta-22 sp-8 an-22 2677 is-8 ta-23 sp-8 an-23 2678 is-8 ta-24 sp-8 an-24 2679 is-8 ta-25 sp-8 an-25 2680 is-8 ta-26 sp-8 an-26 2681 is-8 ta-27 sp-8 an-27 2682 is-8 ta-28 sp-8 an-28 2683 is-8 ta-29 sp-8 an-29 2684 is-8 ta-30 sp-8 an-30 2685 is-8 ta-31 sp-8 an-31 2686 is-8 ta-32 sp-8 an-32 2687 is-8 ta-33 sp-8 an-33 2688 is-8 ta-34 sp-8 an-34 2689 is-8 ta-35 sp-8 an-35 2690 is-8 ta-36 sp-8 an-36 2691 is-8 ta-37 sp-8 an-37 2692 is-8 ta-38 sp-8 an-38 2693 is-8 ta-39 sp-8 an-39 2694 is-8 ta-40 sp-8 an-40 2695 is-8 ta-41 sp-8 an-41 2696 is-8 ta-42 sp-8 an-42 2697 is-8 ta-43 sp-8 an-43 2698 is-8 ta-44 sp-8 an-44 2699 is-8 ta-45 sp-8 an-45 2700 is-8 ta-46 sp-8 an-46 2701 is-8 ta-47 sp-8 an-47 2702 is-8 ta-48 sp-8 an-48 2703 is-8 ta-49 sp-8 an-49 2704 is-8 ta-50 sp-8 an-50 2705 is-8 ta-51 sp-8 an-51 2706 is-8 ta-52 sp-8 an-52 2707 is-8 ta-53 sp-8 an-53 2708 is-8 ta-54 sp-8 an-54 2709 is-8 ta-55 sp-8 an-55 2710 is-8 ta-56 sp-8 an-56 2711 is-8 ta-57 sp-8 an-57 2712 is-8 ta-58 sp-8 an-58 2713 is-8 ta-59 sp-8 an-59 2714 is-8 ta-60 sp-8 an-60 2715 is-8 ta-61 sp-8 an-61 2716 is-8 ta-62 sp-8 an-62 2717 is-8 ta-63 sp-8 an-63 2718 is-8 ta-64 sp-8 an-64 2719 is-8 ta-65 sp-8 an-65 2720 is-8 ta-66 sp-8 an-66 2721 is-8 ta-67 sp-8 an-67 2722 is-8 ta-68 sp-8 an-68 2723 is-8 ta-69 sp-8 an-69 2724 is-8 ta-70 sp-8 an-70 2725 is-8 ta-71 sp-8 an-71 2726 is-8 ta-72 sp-8 an-72 2727 is-8 ta-73 sp-8 an-73 2728 is-8 ta-74 sp-8 an-74 2729 is-8 ta-75 sp-8 an-75 2730 is-8 ta-76 sp-8 an-76 2731 is-8 ta-77 sp-8 an-77 2732 is-8 ta-78 sp-8 an-78 2733 is-8 ta-79 sp-8 an-79 2734 is-8 ta-80 sp-8 an-80 2735 is-8 ta-81 sp-8 an-81 2736 is-8 ta-82 sp-8 an-82 2737 is-8 ta-83 sp-8 an-83 2738 is-8 ta-84 sp-8 an-84 2739 is-8 ta-85 sp-8 an-85 2740 is-8 ta-86 sp-8 an-86 2741 is-8 ta-87 sp-8 an-87 2742 is-8 ta-88 sp-8 an-88 2743 is-8 ta-89 sp-8 an-89 2744 is-8 ta-90 sp-8 an-90 2745 is-8 ta-91 sp-8 an-91 2746 is-8 ta-92 sp-8 an-92 2747 is-8 ta-93 sp-8 an-93 2748 is-8 ta-94 sp-8 an-94 2749 is-8 ta-95 sp-8 an-95 2750 is-8 ta-96 sp-8 an-96 2751 is-8 ta-97 sp-8 an-97 2752 is-8 ta-98 sp-8 an-98 2753 is-8 ta-99 sp-8 an-99 2754 is-8 ta-100 sp-8 an-100 2755 is-8 ta-101 sp-8 an-101 2756 is-8 ta-102 sp-8 an-102 2757 is-8 ta-103 sp-8 an-103 2758 is-8 ta-104 sp-8 an-104 2759 is-8 ta-105 sp-8 an-105 2760 is-8 ta-106 sp-8 an-106 2761 is-8 ta-107 sp-8 an-107 2762 is-8 ta-108 sp-8 an-108 2763 is-8 ta-109 sp-8 an-109 2764 is-8 ta-110 sp-8 an-110 2765 is-8 ta-111 sp-8 an-111 2766 is-8 ta-112 sp-8 an-112 2767 is-8 ta-113 sp-8 an-113 2768 is-8 ta-114 sp-8 an-114 2769 is-8 ta-115 sp-8 an-115 2770 is-8 ta-116 sp-8 an-116 2771 is-8 ta-117 sp-8 an-117 2772 is-8 ta-118 sp-8 an-118 2773 is-8 ta-119 sp-8 an-119 2774 is-8 ta-120 sp-8 an-120 2775 is-8 ta-121 sp-8 an-121 2776 is-8 ta-122 sp-8 an-122 2777 ia-8 ta-123 sp-8 an-123 2778 is-8 ta-124 sp-8 an-124 2779 is-8 ta-125 sp-8 an-125 2780 is-8 ta-126 sp-8 an-126 2781 is-8 ta-127 sp-8 an-127 2782 is-8 ta-128 sp-8 an-128 2783 is-8 ta-129 sp-8 an-129 2784 is-8 ta-130 sp-8 an-130 2785 is-8 ta-131 sp-8 an-131 2786 is-8 ta-132 sp-8 an-132 2787 is-8 ta-133 sp-8 an-133 2788 is-8 ta-134 sp-8 an-134 2789 is-8 ta-135 sp-8 an-135 2790 is-8 ta-136 sp-8 an-136 2791 is-8 ta-137 sp-8 an-137 2792 is-8 ta-138 sp-8 an-138 2793 is-8 ta-139 sp-8 an-139 2794 is-8 ta-140 sp-8 an-140 2795 is-8 ta-141 sp-8 an-141 2796 is-8 ta-142 sp-8 an-142 2797 is-8 ta-143 sp-8 an-143 2798 is-8 ta-144 sp-8 an-144 2799 is-8 ta-145 sp-8 an-145 2800 is-8 ta-146 sp-8 an-146 2801 is-8 ta-147 sp-8 an-147 2802 is-8 ta-148 sp-8 an-148 2803 is-8 ta-149 sp-8 an-149 2804 is-8 ta-150 sp-8 an-150 2805 is-8 ta-151 sp-8 an-151 2806 is-8 ta-152 sp-8 an-152 2807 is-8 ta-153 sp-8 an-153 2808 is-8 ta-154 sp-8 an-154 2809 is-8 ta-155 sp-8 an-155 2810 is-8 ta-156 sp-8 an-156 2811 is-8 ta-157 sp-8 an-157 2812 is-8 ta-158 sp-8 an-158 2813 is-8 ta-159 sp-8 an-159 2814 is-8 ta-160 sp-8 an-160 2815 is-8 ta-161 sp-8 an-161 2816 is-8 ta-162 sp-8 an-162 2817 is-8 ta-163 sp-8 an-163 2818 is-8 ta-164 sp-8 an-164 2819 is-8 ta-165 sp-8 an-165 2820 is-8 ta-166 sp-8 an-166 2821 is-8 ta-167 sp-8 an-167 2822 is-8 ta-168 sp-8 an-168 2823 is-8 ta-169 sp-8 an-169 2824 is-8 ta-170 sp-8 an-170 2825 is-8 ta-171 sp-8 an-171 2826 is-8 ta-172 sp-8 an-172 2827 is-8 ta-173 sp-8 an-173 2828 is-8 ta-174 sp-8 an-174 2829 is-8 ta-175 sp-8 an-175 2830 is-8 ta-176 sp-8 an-176 2831 is-8 ta-177 sp-8 an-177 2832 is-8 ta-178 sp-8 an-178 2833 is-8 ta-179 sp-8 an-179 2834 is-8 ta-180 sp-8 an-180 2835 is-8 ta-181 sp-8 an-181 2836 is-8 ta-182 sp-8 an-182 2837 is-8 ta-183 sp-8 an-183 2838 is-8 ta-184 sp-8 an-184 2839 is-8 ta-185 sp-8 an-185 2840 is-8 ta-186 sp-8 an-186 2841 is-8 ta-187 sp-8 an-187 2842 is-8 ta-188 sp-8 an-188 2843 is-8 ta-189 sp-8 an-189 2844 is-8 ta-190 sp-8 an-190 2845 is-8 ta-191 sp-8 an-191 2846 is-8 ta-192 sp-8 an-192 2847 is-8 ta-193 sp-8 an-193 2848 is-8 ta-194 sp-8 an-194 2849 is-8 ta-195 sp-8 an-195 2850 is-8 ta-196 sp-8 an-196 2851 is-8 ta-197 sp-8 an-197 2852 is-8 ta-198 sp-8 an-198 2853 is-8 ta-199 sp-8 an-199 2854 is-8 ta-200 sp-8 an-200 2855 is-8 ta-201 sp-8 an-201 2856 is-8 ta-202 sp-8 an-202 2857 is-8 ta-203 sp-8 an-203 2858 is-8 ta-204 sp-8 an-204 2859 is-8 ta-205 sp-8 an-205 2860 is-8 ta-206 sp-8 an-206 2861 is-8 ta-207 sp-8 an-207 2862 is-8 ta-208 sp-8 an-208 2863 is-8 ta-209 sp-8 an-209 2864 is-8 ta-210 sp-8 an-210 2865 is-8 ta-211 sp-8 an-211 2866 is-8 ta-212 sp-8 an-212 2867 is-8 ta-213 sp-8 an-213 2868 is-8 ta-214 sp-8 an-214 2869 is-8 ta-215 sp-8 an-215 2870 is-8 ta-216 sp-8 an-216 2871 is-8 ta-217 sp-8 an-217 2872 is-8 ta-218 sp-8 an-218 2873 is-8 ta-219 sp-8 an-219 2874 is-8 ta-220 sp-8 an-220 2875 is-8 ta-221 sp-8 an-221 2876 is-8 ta-222 sp-8 an-222 2877 is-8 ta-223 sp-8 an-223 2878 is-8 ta-224 sp-8 an-224 2879 is-8 ta-225 sp-8 an-225 2880 is-8 ta-226 sp-8 an-226 2881 is-8 ta-227 sp-8 an-227 2882 is-8 ta-228 sp-8 an-228 2833 is-8 ta-229 sp-8 an-229 2884 is-8 ta-230 sp-8 an-230 2885 is-8 ta-231 sp-8 an-231 2886 is-8 ta-232 sp-8 an-232 2887 is-8 ta-233 sp-8 an-233 2888 is-8 ta-234 sp-8 an-234 2889 is-8 ta-235 sp-8 an-235 2890 is-8 ta-236 sp-8 an-236 2891 is-8 ta-237 sp-8 an-237 2892 is-8 ta-238 sp-8 an-238 2893 is-8 ta-239 sp-8 an-239 2894 is-8 ta-240 sp-8 an-240 2895 is-8 ta-241 sp-8 an-241 2896 is-8 ta-242 sp-8 an-242 2897 is-8 ta-243 sp-8 an-243 2898 is-8 ta-244 sp-8 an-244 2899 is-8 ta-245 sp-8 an-245 2900 is-8 ta-246 sp-8 an-246 2901 is-8 ta-247 sp-8 an-247 2902 is-8 ta-248 sp-8 an-248 2903 is-8 ta-249 sp-8 an-249 2904 is-8 ta-250 sp-8 an-250 2905 is-8 ta-251 sp-8 an-251 2906 is-8 ta-252 sp-8 an-252 2907 is-8 ta-253 sp-8 an-253 2908 is-8 ta-254 sp-8 an-254 2909 is-8 ta-255 sp-8 an-255 2910 is-8 ta-256 sp-8 an-256 2911 is-8 ta-257 sp-8 an-257 2912 is-8 ta-258 sp-8 an-258 2913 is-8 ta-259 sp-8 an-259 2914 is-8 ta-260 sp-8 an-260 2915 is-8 ta-261 sp-8 an-261 2916 is-8 ta-262 sp-8 an-262 2917 is-8 ta-263 sp-8 an-263 2918 is-8 ta-264 sp-8 an-264 2919 is-8 ta-265 sp-8 an-265 2920 is-8 ta-266 sp-8 an-266 2921 is-8 ta-267 sp-8 an-267 2922 is-8 ta-268 sp-8 an-268 2923 is-8 ta-269 sp-8 an-269 2924 is-8 ta-270 sp-8 an-270 2925 is-8 ta-271 sp-8 an-271 2926 is-8 ta-272 sp-8 an-272 2927 is-8 ta-273 sp-8 an-273 2928 is-8 ta-274 sp-8 an-274 2929 is-8 ta-275 sp-8 an-275 2930 is-8 ta-276 sp-8 an-276 2931 is-8 ta-277 sp-8 an-277 2932 is-8 ta-278 sp-8 an-278 2933 is-8 ta-279 sp-8 an-279 2934 is-8 ta-280 sp-8 an-280 2935 is-8 ta-281 sp-8 an-281 2936 is-8 ta-282 sp-8 an-282 2937 is-8 ta-283 sp-8 an-283 2938 is-8 ta-284 sp-8 an-284 2939 is-8 ta-285 sp-8 an-285 2940 is-8 ta-286 sp-8 an-286 2941 is-8 ta-287 sp-8 an-287 2942 is-8 ta-288 sp-8 an-288 2943 is-8 ta-289 sp-8 an-289 2944 is-8 ta-290 sp-8 an-290 2945 is-8 ta-291 sp-8 an-291 2946 is-8 ta-292 sp-8 an-292 2947 is-8 ta-293 sp-8 an-293 2948 is-8 ta-294 sp-8 an-294 2949 is-8 ta-295 sp-8 an-295 2950 is-8 ta-296 sp-8 an-296 2951 is-8 ta-297 sp-8 an-297 2952 is-8 ta-298 sp-8 an-298 2953 is-8 ta-299 sp-8 an-299 2954 is-8 ta-300 sp-8 an-300 2955 is-8 ta-301 sp-8 an-301 2956 is-8 ta-302 sp-8 an-302 2957 is-8 ta-303 sp-8 an-303 2958 is-8 ta-304 sp-8 an-304 2959 is-8 ta-305 sp-8 an-305 2960 is-8 ta-306 sp-8 an-306 2961 is-8 ta-307 sp-8 an-307 2962 is-8 ta-308 sp-8 an-308 2963 is-8 ta-309 sp-8 an-309 2964 is-8 ta-310 sp-8 an-310 2965 is-8 ta-311 sp-8 an-311 2966 is-8 ta-312 sp-8 an-312 2967 is-8 ta-313 sp-8 an-313 2968 is-8 ta-314 sp-8 an-314 2969 is-8 ta-315 sp-8 an-315 2970 is-8 ta-316 sp-8 an-316 2971 is-8 ta-317 sp-8 an-317 2972 is-8 ta-318 sp-8 an-318 2973 is-8 ta-319 sp-8 an-319 2974 is-8 ta-320 sp-8 an-320 2975 is-8 ta-321 sp-8 an-321 2976 is-8 ta-322 sp-8 an-322 2977 is-8 ta-323 sp-8 an-323 2978 is-8 ta-324 sp-8 an-324 2979 is-8 ta-325 sp-8 an-325 2980 is-8 ta-326 sp-8 an-326 2981 is-8 ta-327 sp-8 an-327 2982 is-8 ta-328 sp-8 an-328 2983 is-8 ta-329 sp-8 an-329 2984 is-8 ta-330 sp-8 an-330 2985 is-8 ta-331 sp-8 an-331 2986 is-8 ta-332 sp-8 an-332 2987 is-8 ta-333 sp-8 an-333 2988 is-8 ta-334 sp-8 an-334 2989 is-8 ta-335 sp-8 an-335 2990 is-8 ta-336 sp-8 an-336 2991 is-8 ta-337 sp-8 an-337 2992 is-8 ta-338 sp-8 an-338 2993 is-8 ta-339 sp-8 an-339 2994 is-8 ta-340 sp-8 an-340 2995 is-8 ta-341 sp-8 an-341 2996 is-8 ta-342 sp-8 an-342 2997 is-8 ta-343 sp-8 an-343 2998 is-8 ta-344 sp-8 an-344 2999 is-8 ta-345 sp-8 an-345 3000 is-8 ta-346 sp-8 an-346 3001 is-8 ta-347 sp-8 an-347 3002 is-8 ta-348 sp-8 an-348 3003 is-8 ta-349 sp-8 an-349 3004 is-8 ta-350 sp-8 an-350 3005 is-8 ta-351 sp-8 an-351 3006 is-8 ta-352 sp-8 an-352 3007 is-8 ta-353 sp-8 an-353 3008 is-8 ta-354 sp-8 an-354 3009 is-8 ta-355 sp-8 an-355 3010 is-8 ta-356 sp-8 an-356 3011 is-8 ta-357 sp-8 an-357 3012 is-8 ta-358 sp-8 an-358 3013 is-8 ta-359 sp-8 an-359 3014 is-8 ta-360 sp-8 an-360 3015 is-8 ta-361 sp-8 an-361 3016 is-8 ta-362 sp-8 an-362 3017 is-8 ta-363 sp-8 an-363 3018 is-8 ta-364 sp-8 an-364 3019 is-8 ta-365 sp-8 an-365 3020 is-8 ta-366 sp-8 an-366 3021 is-8 ta-367 sp-8 an-367 3022 is-8 ta-368 sp-8 an-368 3023 is-8 ta-369 sp-8 an-369 3024 is-8 ta-370 sp-8 an-370 3025 is-8 ta-371 sp-8 an-371 3026 is-3 ta-372 sp-8 an-372 3027 is-8 ta-373 sp-8 an-373 3028 is-8 ta-374 sp-8 an-374 3029 is-8 ta-375 sp-8 an-375 3030 is-8 ta-376 sp-8 an-376 3031 is-8 ta-377 sp-8 an-377 3032 is-9 ta-1 sp-9 an-1 3033 is-9 ta-2 sp-9 an-2 3034 is-9 ta-3 sp-9 an-3 3035 is-9 ta-4 sp-9 an-4 3036 is-9 ta-5 sp-9 an-5 3037 is-9 ta-6 sp-9 an-6 3038 is-9 ta-7 sp-9 an-7 3039 is-9 ta-8 sp-9 an-8 3040 is-9 ta-9 sp-9 an-9 3041 is-9 ta-10 sp-9 an-10 3042 is-9 ta-11 sp-9 an-11 3043 is-9 ta-12 sp-9 an-12 3044 is-9 ta-13 sp-9 an-13 3045 is-9 ta-14 sp-9 an-14 3046 is-9 ta-15 sp-9 an-15 3047 is-9 ta-16 sp-9 an-16 3048 is-9 ta-17 sp-9 an-17 3049 is-9 ta-18 sp-9 an-18 3050 is-9 ta-19 sp-9 an-19 3051 is-9 ta-20 sp-9 an-20 3052 is-9 ta-21 sp-9 an-21 3053 is-9 ta-22 sp-9 an-22 3054 is-9 ta-23 sp-9 an-23 3055 is-9 ta-24 sp-9 an-24 3056 is-9 ta-25 sp-9 an-25 3057 is-9 ta-26 sp-9 an-26 3058 is-9 ta-27 sp-9 an-27 3059 is-9 ta-28 sp-9 an-28 3060 is-9 ta-29 sp-9 an-29 3061 is-9 ta-30 sp-9 an-30 3062 is-9 ta-31 sp-9 an-31 3063 is-9 ta-32 sp-9 an-32 3064 is-9 ta-33 sp-9 an-33 3065 is-9 ta-34 sp-9 an-34 3066 is-9 ta-35 sp-9 an-35 3067 is-9 ta-36 sp-9 an-36 3068 is-9 ta-37 sp-9 an-37 3069 is-9 ta-38 sp-9 an-38 3070 is-9 ta-39 sp-9 an-39 3071 is-9 ta-40 sp-9 an-40 3072 is-9 ta-41 sp-9 an-41 3073 is-9 ta-42 sp-9 an-42 3074 is-9 ta-43 sp-9 an-43 3075 is-9 ta-44 sp-9 an-44 3076 is-9 ta-45 sp-9 an-45 3077 is-9 ta-46 sp-9 an-46 3078 is-9 ta-47 sp-9 an-47 3079 is-9 ta-48 sp-9 an-48 3080 is-9 ta-49 sp-9 an-49 3081 is-9 ta-50 sp-9 an-50 3082 is-9 ta-51 sp-9 an-51 3083 is-9 ta-52 sp-9 an-52 3084 is-9 ta-53 sp-9 an-53 3085 is-9 ta-54 sp-9 an-54 3086 is-9 ta-55 sp-9 an-55 3087 is-9 ta-56 sp-9 an-56 3088 is-9 ta-57 sp-9 an-57 3089 is-9 ta-58 sp-9 an-58 3090 is-9 ta-59 sp-9 an-59 3091 is-9 ta-60 sp-9 an-60 3092 is-9 ta-61 sp-9 an-61 3093 is-9 ta-62 sp-9 an-62 3094 is-9 ta-63 sp-9 an-63 3095 is-9 ta-64 sp-9 an-64 3096 is-9 ta-65 sp-9 an-65 3097 is-9 ta-66 sp-9 an-66 3098 is-9 ta-67 sp-9 an-67 3099 is-9 ta-68 sp-9 an-68 3100 is-9 ta-69 sp-9 an-69 3101 is-9 ta-70 sp-9 an-70 3102 is-9 ta-71 sp-9 an-71 3103 is-9 ta-72 sp-9 an-72 3104 is-9 ta-73 sp-9 an-73 3105 is-9 ta-74 sp-9 an-74 3106 is-9 ta-75 sp-9 an-75 3107 is-9 ta-76 sp-9 an-76 3108 is-9 ta-77 sp-9 an-77 3109 is-9 ta-78 sp-9 an-78 3110 is-9 ta-79 sp-9 an-79 3111 is-9 ta-80 sp-9 an-80 3112 is-9 ta-81 sp-9 an-81 3113 is-9 ta-82 sp-9 an-82 3114 is-9 ta-83 sp-9 an-83 3115 is-9 ta-84 sp-9 an-84 3116 is-9 ta-85 sp-9 an-85 3117 is-9 ta-86 sp-9 an-86 3118 is-9 ta-87 sp-9 an-87 3119 is-9 ta-88 sp-9 an-88 3120 is-9 ta-89 sp-9 an-89 3121 is-9 ta-90 sp-9 an-90 3122 is-9 ta-91 sp-9 an-91 3123 is-9 ta-92 sp-9 an-92 3124 is-9 ta-93 sp-9 an-93 3125 is-9 ta-94 sp-9 an-94 3126 is-9 ta-95 sp-9 an-95 3127 is-9 ta-96 sp-9 an-96 3128 is-9 ta-97 sp-9 an-97 3129 is-9 ta-98 sp-9 an-98 3130 is-9 ta-99 sp-9 an-99 3131 is-9 ta-100 sp-9 an-100 3132 is-9 ta-101 sp-9 an-101 3133 is-9 ta-102 sp-9 an-102 3134 is-9 ta-103 sp-9 an-103 3135 is-9 ta-104 sp-9 an-104 3136 is-9 ta-105 sp-9 an-105 3137 is-9 ta-106 sp-9 an-106 3138 is-9 ta-107 sp-9 an-107 3139 is-9 ta-108 sp-9 an-108 3140 is-9 ta-109 sp-9 an-109 3141 is-9 ta-110 sp-9 an-110 3142 is-9 ta-111 sp-9 an-111 3143 is-9 ta-112 sp-9 an-112 3144 is-9 ta-113 sp-9 an-113 3145 is-9 ta-114 sp-9 an-114 3146 is-9 ta-115 sp-9 an-115 3147 is-9 ta-116 sp-9 an-116 3148 is-9 ta-117 sp-9 an-117 3149 is-9 ta-118 sp-9 an-118 3150 is-9 ta-119 sp-9 an-119 3151 is-9 ta-120 sp-9 an-120 3152 is-9 ta-121 sp-9 an-121 3153 is-9 ta-122 sp-9 an-122 3154 is-9 ta-123 sp-9 an-123 3155 is-9 ta-124 sp-9 an-124 3156 is-9 ta-125 sp-9 an-125 3157 is-9 ta-126 sp-9 an-126 3158 is-9 ta-127 sp-9 an-127 3159 is-9 ta-128 sp-9 an-128 3160 is-9 ta-129 sp-9 an-129 3161 is-9 ta-130 sp-9 an-130 3162 is-9 ta-131 sp-9 an-131 3163 is-9 ta-132 sp-9 an-132 3164 is-9 ta-133 sp-9 an-133 3165 is-9 ta-134 sp-9 an-134 3166 is-9 ta-135 sp-9 an-135 3167 is-9 ta-136 sp-9 an-136 3168 is-9 ta-137 sp-9 an-137 3169 is-9 ta-138 sp-9 an-138 3170 is-9 ta-139 sp-9 an-139 3171 is-9 ta-140 sp-9 an-140 3172 is-9 ta-141 sp-9 an-141 3173 is-9 ta-142 sp-9 an-142 3174 is-9 ta-143 sp-9 an-143 3175 is-9 ta-144 sp-9 an-144 3176 is-9 ta-145 sp-9 an-145 3177 is-9 ta-146 sp-9 an-146 3178 is-9 ta-147 sp-9 an-147 3179 is-9 ta-148 sp-9 an-148 3180 is-9 ta-149 sp-9 an-149 3181 is-9 ta-150 sp-9 an-150 3182 is-9 ta-151 sp-9 an-151 3183 is-9 ta-152 sp-9 an-152 3184 is-9 ta-153 sp-9 an-153 3185 is-9 ta-154 sp-9 an-154 3186 is-9 ta-155 sp-9 an-155 3187 is-9 ta-156 sp-9 an-156 3188 is-9 ta-157 sp-9 an-157 3189 is-9 ta-158 sp-9 an-158 3190 is-9 ta-159 sp-9 an-159 3191 is-9 ta-160 sp-9 an-160 3192 is-9 ta-161 sp-9 an-161 3193 is-9 ta-162 sp-9 an-162 3194 is-9 ta-163 sp-9 an-163 3195 is-9 ta-164 sp-9 an-164 3196 is-9 ta-165 sp-9 an-165 3197 is-9 ta-166 sp-9 an-166 3198 is-9 ta-167 sp-9 an-167 3199 is-9 ta-168 sp-9 an-168 3200 is-9 ta-169 sp-9 an-169 3201 is-9 ta-170 sp-9 an-170 3202 is-9 ta-171 sp-9 an-171 3203 is-9 ta-172 sp-9 an-172 3204 is-9 ta-173 sp-9 an-173 3205 is-9 ta-174 sp-9 an-174 3206 is-9 ta-175 sp-9 an-175 3207 is-9 ta-176 sp-9 an-176 3208 is-9 ta-177 sp-9 an-177 3209 is-9 ta-178 sp-9 an-178 3210 is-9 ta-179 sp-9 an-179 3211 is-9 ta-180 sp-9 an-180 3212 is-9 ta-181 sp-9 an-181 3213 is-9 ta-182 sp-9 an-182 3214 is-9 ta-183 sp-9 an-183 3215 is-9 ta-184 sp-9 an-184 3216 is-9 ta-185 sp-9 an-185 3217 is-9 ta-186 sp-9 an-186 3218 is-9 ta-187 sp-9 an-187 3219 is-9 ta-188 sp-9 an-188 3220 is-9 ta-189 sp-9 an-189 3221 is-9 ta-190 sp-9 an-190 3222 is-9 ta-191 sp-9 an-191 3223 is-9 ta-192 sp-9 an-192 3224 is-9 ta-193 sp-9 an-193 3225 is-9 ta-194 sp-9 an-194 3226 is-9 ta-195 sp-9 an-195 3227 is-9 ta-196 sp-9 an-196 3228 is-9 ta-197 sp-9 an-197 3229 is-9 ta-198 sp-9 an-198 3230 is-9 ta-199 sp-9 an-199 3231 is-9 ta-200 sp-9 an-200 3232 is-9 ta-201 sp-9 an-201 3233 is-9 ta-202 sp-9 an-202 3234 is-9 ta-203 sp-9 an-203 3235 is-9 ta-204 sp-9 an-204 3236 is-9 ta-205 sp-9 an-205 3237 is-9 ta-206 sp-9 an-206 3238 is-9 ta-207 sp-9 an-207 3239 is-9 ta-208 sp-9 an-208 3240 is-9 ta-209 sp-9 an-209 3241 is-9 ta-210 sp-9 an-210 3242 is-9 ta-211 sp-9 an-211 3243 is-9 ta-212 sp-9 an-212 3244 is-9 ta-213 sp-9 an-213 3245 is-9 ta-214 sp-9 an-214 3246 is-9 ta-215 sp-9 an-215 3247 is-9 ta-216 sp-9 an-216 3248 is-9 ta-217 sp-9 an-217 3249 is-9 ta-218 sp-9 an-218 3250 is-9 ta-219 sp-9 an-219 3251 is-9 ta-220 sp-9 an-220 3252 is-9 ta-221 sp-9 an-221 3253 is-9 ta-222 sp-9 an-222 3254 is-9 ta-223 sp-9 an-223 3255 is-9 ta-224 sp-9 an-224 3256 is-9 ta-225 sp-9 an-225 3257 is-9 ta-226 sp-9 an-226 3258 is-9 ta-227 sp-9 an-227 3259 is-9 ta-228 sp-9 an-228 3260 is-9 ta-229 sp-9 an-229 3261 is-9 ta-230 sp-9 an-230 3262 is-9 ta-231 sp-9 an-231 3263 is-9 ta-232 sp-9 an-232 3264 is-9 ta-233 sp-9 an-233 3265 is-9 ta-234 sp-9 an-234 3266 is-9 ta-235 sp-9 an-235 3267 is-9 ta-236 sp-9 an-236 3268 is-9 ta-237 sp-9 an-237 3269 is-9 ta-238 sp-9 an-238 3270 is-9 ta-239 sp-9 an-239 3271 is-9 ta-240 sp-9 an-240 3272 is-9 ta-241 sp-9 an-241 3273 is-9 ta-242 sp-9 an-242 3274 is-9 ta-243 sp-9 an-243 3275 is-9 ta-244 sp-9 an-244 3276 is-9 ta-245 sp-9 an-245 3277 is-9 ta-246 sp-9 an-246 3278 is-9 ta-247 sp-9 an-247 3279 is-9 ta-248 sp-9 an-248 3280 is-9 ta-249 sp-9 an-249 3281 is-9 ta-250 sp-9 an-250 3282 is-9 ta-251 sp-9 an-251 3283 is-9 ta-252 sp-9 an-252 3284 is-9 ta-253 sp-9 an-253 3285 is-9 ta-254 sp-9 an-254 3286 is-9 ta-255 sp-9 an-255 3287 is-9 ta-256 sp-9 an-256 3288 is-9 ta-257 sp-9 an-257 3289 is-9 ta-258 sp-9 an-258 3290 is-9 ta-259 sp-9 an-259 3291 is-9 ta-260 sp-9 an-260 3292 is-9 ta-261 sp-9 an-261 3293 is-9 ta-262 sp-9 an-262 3294 is-9 ta-263 sp-9 an-263 3295 is-9 ta-264 sp-9 an-264 3296 is-9 ta-265 sp-9 an-265 3297 is-9 ta-266 sp-9 an-266 3298 is-9 ta-267 sp-9 an-267 3299 is-9 ta-268 sp-9 an-268 3300 is-9 ta-269 sp-9 an-269 3301 is-9 ta-270 sp-9 an-270 3302 is-9 ta-271 sp-9 an-271 3303 is-9 ta-272 sp-9 an-272 3304 is-9 ta-273 sp-9 an-273 3305 is-9 ta-274 sp-9 an-274 3306 is-9 ta-275 sp-9 an-275 3307 is-9 ta-276 sp-9 an-276 3308 is-9 ta-277 sp-9 an-277 3309 is-9 ta-278 sp-9 an-273 3310 is-9 ta-279 sp-9 an-279 3311 is-9 ta-280 sp-9 an-280 3312 is-9 ta-281 sp-9 an-281 3313 is-9 ta-282 sp-9 an-282 3314 is-9 ta-283 sp-9 an-283 3315 is-9 ta-284 sp-9 an-284 3316 is-9 ta-285 sp-9 an-285 3317 is-9 ta-286 sp-9 an-286 3318 is-9 ta-287 sp-9 an-287 3319 is-9 ta-288 sp-9 an-288 3320 is-9 ta-289 sp-9 an-289 3321 is-9 ta-290 sp-9 an-290 3322 is-9 ta-291 sp-9 an-291 3323 is-9 ta-292 sp-9 an-292 3324 is-9 ta-293 sp-9 an-293 3325 is-9 ta-294 sp-9 an-294 3326 is-9 ta-295 sp-9 an-295 3327 is-9 ta-296 sp-9 an-296 3328 is-9 ta-297 sp-9 an-297 3329 is-9 ta-298 sp-9 an-298 3330 is-9 ta-299 sp-9 an-299 3331 is-9 ta-300 sp-9 an-300 3332 is-9 ta-301 sp-9 an-301 3333 is-9 ta-302 sp-9 an-302 3334 is-9 ta-303 sp-9 an-303 3335 is-9 ta-304 sp-9 an-304 3336 is-9 ta-305 sp-9 an-305 3337 is-9 ta-306 sp-9 an-306 3338 is-9 ta-307 sp-9 an-307 3339 is-9 ta-308 sp-9 an-308 3340 is-9 ta-309 sp-9 an-309 3341 is-9 ta-310 sp-9 an-310 3342 is-9 ta-311 sp-9 an-311 3343 is-9 ta-312 sp-9 an-312 3344 is-9 ta-313 sp-9 an-313 3345 is-9 ta-314 sp-9 an-314 3346 is-9 ta-315 sp-9 an-315 3347 is-9 ta-316 sp-9 an-316 3348 is-9 ta-317 sp-9 an-317 3349 is-9 ta-318 sp-9 an-318 3350 is-9 ta-319 sp-9 an-319 3351 is-9 ta-320 sp-9 an-320 3352 is-9 ta-321 sp-9 an-321 3353 is-9 ta-322 sp-9 an-322 3354 is-9 ta-323 sp-9 an-323 3355 is-9 ta-324 sp-9 an-324 3356 is-9 ta-325 sp-9 an-325 3357 is-9 ta-326 sp-9 an-326 3358 is-9 ta-327 sp-9 an-327 3359 is-9 ta-328 sp-9 an-328 3360 is-9 ta-329 sp-9 an-329 3361 is-9 ta-330 sp-9 an-330 3362 is-9 ta-331 sp-9 an-331 3363 is-9 ta-332 sp-9 an-332 3364 is-9 ta-333 sp-9 an-333 3365 is-9 ta-334 sp-9 an-334 3366 is-9 ta-335 sp-9 an-335 3367 is-9 ta-336 sp-9 an-336 3368 is-9 ta-337 sp-9 an-337 3369 is-9 ta-338 sp-9 an-338 3370 is-9 ta-339 sp-9 an-339 3371 is-9 ta-340 sp-9 an-340 3372 is-9 ta-341 sp-9 an-341 3373 is-9 ta-342 sp-9 an-342 3374 is-9 ta-343 sp-9 an-343 3375 is-9 ta-344 sp-9 an-344 3376 is-9 ta-345 sp-9 an-345 3377 is-9 ta-346 sp-9 an-346 3378 is-9 ta-347 sp-9 an-347 3379 is-9 ta-348 sp-9 an-348 3380 is-9 ta-349 sp-9 an-349 3381 is-9 ta-350 sp-9 an-350 3382 is-9 ta-351 sp-9 an-351 3383 is-9 ta-352 sp-9 an-352 3384 is-9 ta-353 sp-9 an-353 3385 is-9 ta-354 sp-9 an-354 3386 is-9 ta-355 sp-9 an-355 3387 is-9 ta-356 sp-9 an-356 3388 is-9 ta-357 sp-9 an-357 3389 is-9 ta-358 sp-9 an-358 3390 is-9 ta-359 sp-9 an-359 3391 is-9 ta-360 sp-9 an-360 3392 is-9 ta-361 sp-9 an-361 3393 is-9 ta-362 sp-9 an-362 3394 is-9 ta-363 sp-9 an-363 3395 is-9 ta-364 sp-9 an-364 3396 is-9 ta-365 sp-9 an-365 3397 is-9 ta-366 sp-9 an-366 3398 is-9 ta-367 sp-9 an-367 3399 is-9 ta-368 sp-9 an-368 3400 is-9 ta-369 sp-9 an-369 3401 is-9 ta-370 sp-9 an-370 3402 is-9 ta-371 sp-9 an-371 3403 is-9 ta-372 sp-9 an-372 3404 is-9 ta-373 sp-9 an-373 3405 is-9 ta-374 sp-9 an-374 3406 is-9 ta-375 sp-9 an-375 3407 is-9 ta-376 sp-9 an-376 3408 is-9 ta-377 sp-9 an-377 3409 is-14 ta-1 sp-14 an-1 3410 is-14 ta-2 sp-14 an-2 3411 is-14 ta-3 sp-14 an-3 3412 is-14 ta-4 sp-14 an-4 3413 is-14 ta-5 sp-14 an-5 3414 is-14 ta-6 sp-14 an-6 3415 is-14 ta-7 sp-14 an-7 3416 is-14 ta-8 sp-14 an-8 3417 is-14 ta-9 sp-14 an-9 3418 is-14 ta-10 sp-14 an-10 3419 is-14 ta-11 sp-14 an-11 3420 is-14 ta-12 sp-14 an-12 3421 is-14 ta-13 sp-14 an-13 3422 is-14 ta-14 sp-14 an-14 3423 is-14 ta-15 sp-14 an-15 3424 is-14 ta-16 sp-14 an-16 3425 is-14 ta-17 sp-14 an-17 3426 is-14 ta-18 sp-14 an-18 3427 is-14 ta-19 sp-14 an-19 3428 is-14 ta-20 sp-14 an-20 3429 is-14 ta-21 sp-14 an-21 3430 is-14 ta-22 sp-14 an-22 3431 is-14 ta-23 sp-14 an-23 3432 is-14 ta-24 sp-14 an-24 3433 is-14 ta-25 sp-14 an-25 3434 is-14 ta-26 sp-14 an-26 3435 is-14 ta-27 sp-14 an-27 3436 is-14 ta-28 sp-14 an-28 3437 is-14 ta-29 sp-14 an-29 3438 is-14 ta-30 sp-14 an-30 3439 is-14 ta-31 sp-14 an-31 3440 is-14 ta-32 sp-14 an-32 3441 is-14 ta-33 sp-14 an-33 3442 is-14 ta-34 sp-14 an-34 3443 is-14 ta-35 sp-14 an-35 3444 is-14 ta-36 sp-14 an-36 3445 is-14 ta-37 sp-14 an-37 3446 is-14 ta-38 sp-14 an-38 3447 is-14 ta-39 sp-14 an-39 3448 is-14 ta-40 sp-14 an-40 3449 is-14 ta-41 sp-14 an-41 3450 is-14 ta-42 sp-14 an-42 3451 is-14 ta-43 sp-14 an-43 3452 is-14 ta-44 sp-14 an-44 3453 is-14 ta-45 sp-14 an-45 3454 is-14 ta-46 sp-14 an-46 3455 is-14 ta-47 sp-14 an-47 3456 is-14 ta-48 sp-14 an-48 3457 is-14 ta-49 sp-14 an-49 3458 is-14 ta-50 sp-14 an-50 3459 is-14 ta-51 sp-14 an-51 3460 is-14 ta-52 sp-14 an-52 3461 is-14 ta-53 sp-14 an-53 3462 is-14 ta-54 sp-14 an-54 3463 is-14 ta-55 sp-14 an-55 3464 is-14 ta-56 sp-14 an-56 3465 is-14 ta-57 sp-14 an-57 3466 is-14 ta-58 sp-14 an-58 3467 is-14 ta-59 sp-14 an-59 3468 is-14 ta-60 sp-14 an-60 3469 is-14 ta-61 sp-14 an-61 3470 is-14 ta-62 sp-14 an-62 3471 is-14 ta-63 sp-14 an-63 3472 is-14 ta-64 sp-14 an-64 3473 is-14 ta-65 sp-14 an-65 3474 is-14 ta-66 sp-14 an-66 3475 is-14 ta-67 sp-14 an-67 3476 is-14 ta-68 sp-14 an-68 3477 is-14 ta-69 sp-14 an-69 3478 is-14 ta-70 sp-14 an-70 3479 is-14 ta-71 sp-14 an-71 3480 is-14 ta-72 sp-14 an-72 3481 is-14 ta-73 sp-14 an-73 3482 is-14 ta-74 sp-14 an-74 3483 is-14 ta-75 sp-14 an-75 3484 is-14 ta-76 sp-14 an-76 3485 is-14 ta-77 sp-14 an-77 3486 is-14 ta-78 sp-14 an-78 3487 is-14 ta-79 sp-14 an-79 3488 is-14 ta-80 sp-14 an-80 3489 is-14 ta-81 sp-14 an-81 3490 is-14 ta-82 sp-14 an-82 3491 is-14 ta-83 sp-14 an-83 3492 is-14 ta-84 sp-14 an-84 3493 is-14 ta-85 sp-14 an-85 3494 is-14 ta-86 sp-14 an-86 3495 is-14 ta-87 sp-14 an-87 3496 is-14 ta-88 sp-14 an-88 3497 is-14 ta-89 sp-14 an-89 3498 is-14 ta-90 sp-14 an-90 3499 is-14 ta-91 sp-14 an-91 3500 is-14 ta-92 sp-14 an-92 3501 is-14 ta-93 sp-14 an-93 3502 is-14 ta-94 sp-14 an-94 3503 is-14 ta-95 sp-14 an-95 3504 is-14 ta-96 sp-14 an-96 3505 is-14 ta-97 sp-14 an-97 3506 is-14 ta-98 sp-14 an-98 3507 is-14 ta-99 sp-14 an-99 3508 is-14 ta-100 sp-14 an-100 3509 is-14 ta-101 sp-14 an-101 3510 is-14 ta-102 sp-14 an-102 3511 is-14 ta-103 sp-14 an-103 3512 is-14 ta-104 sp-14 an-104 3513 is-14 ta-105 sp-14 an-105 3514 is-14 ta-106 sp-14 an-106 3515 is-14 ta-107 sp-14 an-107 3516 is-14 ta-108 sp-14 an-108 3517 is-14 ta-109 sp-14 an-109 3518 is-14 ta-110 sp-14 an-110 3519 is-14 ta-111 sp-14 an-111 3520 is-14 ta-112 sp-14 an-112 3521 is-14 ta-113 sp-14 an-113 3522 is-14 ta-114 sp-14 an-114 3523 is-14 ta-115 sp-14 an-115 3524 is-14 ta-116 sp-14 an-116 3525 is-14 ta-117 sp-14 an-117 3526 is-14 ta-118 sp-14 an-118 3527 is-14 ta-119 sp-14 an-119 3528 is-14 ta-120 sp-14 an-120 3529 is-14 ta-121 sp-14 an-121 3530 is-14 ta-122 sp-14 an-122 3531 is-14 ta-123 sp-14 an-123 3532 is-14 ta-124 sp-14 an-124 3533 is-14 ta-125 sp-14 an-125 3534 is-14 ta-126 sp-14 an-126 3535 is-14 ta-127 sp-14 an-127 3536 is-14 ta-128 sp-14 an-128 3537 is-14 ta-129 sp-14 an-129 3538 is-14 ta-130 sp-14 an-130 3539 is-14 ta-131 sp-14 an-131 3540 is-14 ta-132 sp-14 an-132 3541 is-14 ta-133 sp-14 an-133 3542 is-14 ta-134 sp-14 an-134 3543 is-14 ta-135 sp-14 an-135 3544 is-14 ta-136 sp-14 an-136 3545 is-14 ta-137 sp-14 an-137 3546 is-14 ta-138 sp-14 an-138 3547 is-14 ta-139 sp-14 an-139 3548 is-14 ta-140 sp-14 an-140 3549 is-14 ta-141 sp-14 an-141 3550 is-14 ta-142 sp-14 an-142 3551 is-14 ta-143 sp-14 an-143 3552 is-14 ta-144 sp-14 an-144 3553 is-14 ta-145 sp-14 an-145 3554 is-14 ta-146 sp-14 an-146 3555 is-14 ta-147 sp-14 an-147 3556 is-14 ta-148 sp-14 an-148 3557 is-14 ta-149 sp-14 an-149 3558 is-14 ta-150 sp-14 an-150 3559 is-14 ta-151 sp-14 an-151 3560 is-14 ta-152 sp-14 an-152 3561 is-14 ta-153 sp-14 an-153 3562 is-14 ta-154 sp-14 an-154 3563 is-14 ta-155 sp-14 an-155 3564 is-14 ta-156 sp-14 an-156 3565 is-14 ta-157 sp-14 an-157 3566 is-14 ta-158 sp-14 an-158 3567 is-14 ta-159 sp-14 an-159 3568 is-14 ta-160 sp-14 an-160 3569 is-14 ta-161 sp-14 an-161 3570 is-14 ta-162 sp-14 an-162 3571 is-14 ta-163 sp-14 an-163 3572 is-14 ta-164 sp-14 an-164 3573 is-14 ta-165 sp-14 an-165 3574 is-14 ta-166 sp-14 an-166 3575 is-14 ta-167 sp-14 an-167 3576 is-14 ta-168 sp-14 an-168 3577 is-14 ta-169 sp-14 an-169 3578 is-14 ta-170 sp-14 an-170 3579 is-14 ta-171 sp-14 an-171 3580 is-14 ta-172 sp-14 an-172 3581 is-14 ta-173 sp-14 an-173 3582 is-14 ta-174 sp-14 an-174 3583 is-14 ta-175 sp-14 an-175 3584 is-14 ta-176 sp-14 an-176 3585 is-14 ta-177 sp-14 an-177 3586 is-14 ta-178 sp-14 an-178 3587 is-14 ta-179 sp-14 an-179 3588 is-14 ta-180 sp-14 an-180 3589 is-14 ta-181 sp-14 an-181 3590 is-14 ta-182 sp-14 an-182 3591 is-14 ta-183 sp-14 an-183 3592 is-14 ta-184 sp-14 an-184 3593 is-14 ta-185 sp-14 an-185 3594 is-14 ta-186 sp-14 an-186 3595 is-14 ta-187 sp-14 an-187 3596 is-14 ta-188 sp-14 an-188 3597 is-14 ta-189 sp-14 an-189 3598 is-14 ta-190 sp-14 an-190 3599 is-14 ta-191 sp-14 an-191 3600 is-14 ta-192 sp-14 an-192 3601 is-14 ta-193 sp-14 an-193 3602 is-14 ta-194 sp-14 an-194 3603 is-14 ta-195 sp-14 an-195 3604 is-14 ta-196 sp-14 an-196 3605 is-14 ta-197 sp-14 an-197 3606 is-14 ta-198 sp-14 an-198 3607 is-14 ta-199 sp-14 an-199 3608 is-14 ta-200 sp-14 an-200 3609 is-14 ta-201 sp-14 an-201 3610 is-14 ta-202 sp-14 an-202 3611 is-14 ta-203 sp-14 an-203 3612 is-14 ta-204 sp-14 an-204 3613 is-14 ta-205 sp-14 an-205 3614 is-14 ta-206 sp-14 an-206 3615 is-14 ta-207 sp-14 an-207 3616 is-14 ta-208 sp-14 an-208 3617 is-14 ta-209 sp-14 an-209 3618 is-14 ta-210 sp-14 an-210 3619 is-14 ta-211 sp-14 an-211 3620 is-14 ta-212 sp-14 an-212 3621 is-14 ta-213 sp-14 an-213 3622 is-14 ta-214 sp-14 an-214 3623 is-14 ta-215 sp-14 an-215 3624 is-14 ta-216 sp-14 an-216 3625 is-14 ta-217 sp-14 an-217 3626 is-14 ta-218 sp-14 an-218 3627 is-14 ta-219 sp-14 an-219 3628 is-14 ta-220 sp-14 an-220 3629 is-14 ta-221 sp-14 an-221 3630 is-14 ta-222 sp-14 an-222 3631 is-14 ta-223 sp-14 an-223 3632 is-14 ta-224 sp-14 an-224 3633 is-14 ta-225 sp-14 an-225 3634 is-14 ta-226 sp-14 an-226 3635 is-14 ta-227 sp-14 an-227 3636 is-14 ta-228 sp-14 an-228 3637 is-14 ta-229 sp-14 an-229 3638 is-14 ta-230 sp-14 an-230 3639 is-14 ta-231 sp-14 an-231 3640 is-14 ta-232 sp-14 an-232 3641 is-14 ta-233 sp-14 an-233 3642 is-14 ta-234 sp-14 an-234 3643 is-14 ta-235 sp-14 an-235 3644 is-14 ta-236 sp-14 an-236 3645 is-14 ta-237 sp-14 an-237 3646 is-14 ta-238 sp-14 an-238 3647 is-14 ta-239 sp-14 an-239 3648 is-14 ta-240 sp-14 an-240 3649 is-14 ta-241 sp-14 an-241 3650 is-14 ta-242 sp-14 an-242 3651 is-14 ta-243 sp-14 an-243 3652 is-14 ta-244 sp-14 an-244 3653 is-14 ta-245 sp-14 an-245 3654 is-14 ta-246 sp-14 an-246 3655 is-14 ta-247 sp-14 an-247 3656 is-14 ta-248 sp-14 an-248 3657 is-14 ta-249 sp-14 an-249 3658 is-14 ta-250 sp-14 an-250 3659 is-14 ta-251 sp-14 an-251 3660 is-14 ta-252 sp-14 an-252 3661 is-14 ta-253 sp-14 an-253 3662 is-14 ta-254 sp-14 an-254 3663 is-14 ta-255 sp-14 an-255 3664 is-14 ta-256 sp-14 an-256 3665 is-14 ta-257 sp-14 an-257 3666 is-14 ta-258 sp-14 an-258 3667 is-14 ta-259 sp-14 an-259 3668 is-14 ta-260 sp-14 an-260 3669 is-14 ta-261 sp-14 an-261 3670 is-14 ta-262 sp-14 an-262 3671 is-14 ta-263 sp-14 an-263 3672 is-14 ta-264 sp-14 an-264 3673 is-14 ta-265 sp-14 an-265 3674 is-14 ta-266 sp-14 an-266 3675 is-14 ta-267 sp-14 an-267 3676 is-14 ta-268 sp-14 an-268 3677 is-14 ta-269 sp-14 an-269 3678 is-14 ta-270 sp-14 an-270 3679 is-14 ta-271 sp-14 an-271 3680 is-14 ta-272 sp-14 an-272 3681 is-14 ta-273 sp-14 an-273 3682 is-14 ta-274 sp-14 an-274 3683 is-14 ta-275 sp-14 an-275 3684 is-14 ta-276 sp-14 an-276 3685 is-14 ta-277 sp-14 an-277 3686 is-14 ta-278 sp-14 an-278 3687 is-14 ta-279 sp-14 an-279 3688 is-14 ta-280 sp-14 an-280 3689 is-14 ta-281 sp-14 an-281 3690 is-14 ta-282 sp-14 an-282 3691 is-14 ta-283 sp-14 an-283 3692 is-14 ta-284 sp-14 an-284 3693 is-14 ta-285 sp-14 an-285 3694 is-14 ta-286 sp-14 an-286 3695 is-14 ta-287 sp-14 an-287 3696 is-14 ta-288 sp-14 an-288 3697 is-14 ta-289 sp-14 an-289 3698 is-14 ta-290 sp-14 an-290 3699 is-14 ta-291 sp-14 an-291 3700 is-14 ta-292 sp-14 an-292 3701 is-14 ta-293 sp-14 an-293 3702 is-14 ta-294 sp-14 an-294 3703 is-14 ta-295 sp-14 an-295 3704 is-14 ta-296 sp-14 an-296 3705 is-14 ta-297 sp-14 an-297 3706 is-14 ta-298 sp-14 an-298 3707 is-14 ta-299 sp-14 an-299 3708 is-14 ta-300 sp-14 an-300 3709 is-14 ta-301 sp-14 an-301 3710 is-14 ta-302 sp-14 an-302 3711 is-14 ta-303 sp-14 an-303 3712 is-14 ta-304 sp-14 an-304 3713 is-14 ta-305 sp-14 an-305 3714 is-14 ta-306 sp-14 an-306 3715 is-14 ta-307 sp-14 an-307 3716 is-14 ta-308 sp-14 an-308 3717 is-14 ta-309 sp-14 an-309 3718 is-14 ta-310 sp-14 an-310 3719 is-14 ta-311 sp-14 an-311 3720 is-14 ta-312 sp-14 an-312 3721 is-14 ta-313 sp-14 an-313 3722 is-14 ta-314 sp-14 an-314 3723 is-14 ta-315 sp-14 an-315 3724 is-14 ta-316 sp-14 an-316 3725 is-14 ta-317 sp-14 an-317 3726 is-14 ta-318 sp-14 an-318 3727 is-14 ta-319 sp-14 an-319 3728 is-14 ta-320 sp-14 an-320 3729 is-14 ta-321 sp-14 an-321 3730 is-14 ta-322 sp-14 an-322 3731 is-14 ta-323 sp-14 an-323 3732 is-14 ta-324 sp-14 an-324 3733 is-14 ta-325 sp-14 an-325 3734 is-14 ta-326 sp-14 an-326 3735 is-14 ta-327 sp-14 an-327 3736 is-14 ta-328 sp-14 an-328 3737 is-14 ta-329 sp-14 an-329 3738 is-14 ta-330 sp-14 an-330 3739 is-14 ta-331 sp-14 an-331 3740 is-14 ta-332 sp-14 an-332 3741 is-14 ta-333 sp-14 an-333 3742 is-14 ta-334 sp-14 an-334 3743 is-14 ta-335 sp-14 an-335 3744 is-14 ta-336 sp-14 an-336 3745 is-14 ta-337 sp-14 an-337 3746 is-14 ta-338 sp-14 an-338 3747 is-14 ta-339 sp-14 an-339 3748 is-14 ta-340 sp-14 an-340 3749 is-14 ta-341 sp-14 an-341 3750 is-14 ta-342 sp-14 an-342 3751 is-14 ta-343 sp-14 an-343 3752 is-14 ta-344 sp-14 an-344 3753 is-14 ta-345 sp-14 an-345 3754 is-14 ta-346 sp-14 an-346 3755 is-14 ta-347 sp-14 an-347 3756 is-14 ta-348 sp-14 an-348 3757 is-14 ta-349 sp-14 an-349 3758 is-14 ta-350 sp-14 an-350 3759 is-14 ta-351 sp-14 an-351 3760 is-14 ta-352 sp-14 an-352 3761 is-14 ta-353 sp-14 an-353 3762 is-14 ta-354 sp-14 an-354 3763 is-14 ta-355 sp-14 an-355 3764 is-14 ta-356 sp-14 an-356 3765 is-14 ta-357 sp-14 an-357 3766 is-14 ta-358 sp-14 an-358 3767 is-14 ta-359 sp-14 an-359 3768 is-14 ta-360 sp-14 an-360 3769 is-14 ta-361 sp-14 an-361 3770 is-14 ta-362 sp-14 an-362 3771 is-14 ta-363 sp-14 an-363 3772 is-14 ta-364 sp-14 an-364 3773 is-14 ta-365 sp-14 an-365 3774 is-14 ta-366 sp-14 an-366 3775 is-14 ta-367 sp-14 an-367 3776 is-14 ta-368 sp-14 an-368 3777 is-14 ta-369 sp-14 an-369 3778 is-14 ta-370 sp-14 an-370 3779 is-14 ta-371 sp-14 an-371 3780 is-14 ta-372 sp-14 an-372 3781 is-14 ta-373 sp-14 an-373 3782 is-14 ta-374 sp-14 an-374 3783 is-14 ta-375 sp-14 an-375 3784 is-14 ta-376 sp-14 an-376 3785 is-14 ta-377 sp-14 an-377 4067 is-1 ta-378 sp-1 an-378 4068 is-1 ta-379 sp-1 an-379 4069 is-1 ta-380 sp-1 an-380 4070 is-1 ta-381 sp-1 an-381 4071 is-1 ta-382 sp-1 an-382 4072 is-1 ta-383 sp-1 an-383 4073 is-1 ta-384 sp-1 an-384 4074 is-1 ta-385 sp-1 an-385 4075 is-1 ta-386 sp-1 an-386 4076 is-1 ta-387 sp-1 an-387 4077 is-1 ta-388 sp-1 an-388 4078 is-1 ta-389 sp-1 an-389 4079 is-1 ta-390 sp-1 an-390 4080 is-1 ta-391 sp-1 an-391 4081 is-1 ta-392 sp-1 an-392 4082 is-1 ta-393 sp-1 an-393 4083 is-2 ta-378 sp-2 an-378 4084 is-2 ta-379 sp-2 an-379 4085 is-2 ta-380 sp-2 an-380 4086 is-2 ta-381 sp-2 an-381 4087 is-2 ta-382 sp-2 an-382 4088 is-2 ta-383 sp-2 an-383 4089 is-2 ta-384 sp-2 an-384 4090 is-2 ta-385 sp-2 an-385 4091 is-2 ta-386 sp-2 an-386 4092 is-2 ta-387 sp-2 an-387 4093 is-2 ta-388 sp-2 an-388 4094 is-2 ta-389 sp-2 an-389 4095 is-2 ta-390 sp-2 an-390 4096 is-2 ta-391 sp-2 an-391 4097 is-2 ta-392 sp-2 an-392 4098 is-2 ta-393 sp-2 an-393 4099 is-3 ta-378 sp-3 an-378 4100 is-3 ta-379 sp-3 an-379 4101 is-3 ta-380 sp-3 an-380 4102 is-3 ta-381 sp-3 an-381 4103 is-3 ta-382 sp-3 an-382 4104 is-3 ta-383 sp-3 an-383 4105 is-3 ta-384 sp-3 an-384 4106 is-3 ta-385 sp-3 an-385 4107 is-3 ta-386 sp-3 an-386 4108 is-3 ta-387 sp-3 an-387 4109 is-3 ta-388 sp-3 an-388 4110 is-3 ta-389 sp-3 an-389 4111 is-3 ta-390 sp-3 an-390 4112 is-3 ta-391 sp-3 an-391 4113 is-3 ta-392 sp-3 an-392 4114 is-3 ta-393 sp-3 an-393 4115 is-4 ta-378 sp-4 an-378 4116 is-4 ta-379 sp-4 an-379 4117 is-4 ta-380 sp-4 an-380 4118 is-4 ta-381 sp-4 an-381 4119 is-4 ta-382 sp-4 an-382 4120 is-4 ta-383 sp-4 an-383 4121 is-4 ta-384 sp-4 an-384 4122 is-4 ta-385 sp-4 an-385 4123 is-4 ta-386 sp-4 an-386 4124 is-4 ta-387 sp-4 an-387 4125 is-4 ta-388 sp-4 an-388 4126 is-4 ta-389 sp-4 an-389 4127 is-4 ta-390 sp-4 an-390 4128 is-4 ta-391 sp-4 an-391 4129 is-4 ta-392 sp-4 an-392 4130 is-4 ta-393 sp-4 an-393 4131 is-5 ta-378 sp-5 an-378 4132 is-5 ta-379 sp-5 an-379 4133 is-5 ta-380 sp-5 an-380 4134 is-5 ta-381 sp-5 an-381 4135 is-5 ta-382 sp-5 an-382 4136 is-5 ta-383 sp-5 an-383 4137 is-5 ta-384 sp-5 an-384 4138 is-5 ta-385 sp-5 an-385 4139 is-5 ta-386 sp-5 an-386 4140 is-5 ta-387 sp-5 an-387 4141 is-5 ta-388 sp-5 an-388 4142 is-5 ta-389 sp-5 an-389 4143 is-5 ta-390 sp-5 an-390 4144 is-5 ta-391 sp-5 an-391 4145 is-5 ta-392 sp-5 an-392 4146 is-5 ta-393 sp-5 an-393 4146 is-6 ta-378 sp-6 an-378 4147 is-6 ta-379 sp-6 an-379 4148 is-6 ta-380 sp-6 an-380 4149 is-6 ta-381 sp-6 an-381 4150 is-6 ta-382 sp-6 an-382 4151 is-6 ta-383 sp-6 an-383 4152 is-6 ta-384 sp-6 an-384 4153 is-6 ta-385 sp-6 an-385 4154 is-6 ta-386 sp-6 an-386 4155 is-6 ta-387 sp-6 an-387 4156 is-6 ta-388 sp-6 an-388 4157 is-6 ta-389 sp-6 an-389 4158 is-6 ta-390 sp-6 an-390 4159 is-6 ta-391 sp-6 an-391 4160 is-6 ta-392 sp-6 an-392 4161 is-6 ta-393 sp-6 an-393 4162 is-7 ta-378 sp-7 an-378 4163 is-7 ta-379 sp-7 an-379 4164 is-7 ta-380 sp-7 an-380 4165 is-7 ta-381 sp-7 an-381 4166 is-7 ta-382 sp-7 an-382 4167 is-7 ta-383 sp-7 an-383 4168 is-7 ta-384 sp-7 an-384 4169 is-7 ta-385 sp-7 an-385 4170 is-7 ta-386 sp-7 an-386 4171 is-7 ta-387 sp-7 an-387 4172 is-7 ta-388 sp-7 an-388 4173 is-7 ta-389 sp-7 an-389 4174 is-7 ta-390 sp-7 an-390 4175 is-7 ta-391 sp-7 an-391 4176 is-7 ta-392 sp-7 an-392 4177 is-7 ta-393 sp-7 an-393 4178 is-8 ta-378 sp-8 an-378 4179 is-8 ta-379 sp-8 an-379 4180 is-8 ta-380 sp-8 an-380 4181 is-8 ta-381 sp-8 an-381 4182 is-8 ta-382 sp-8 an-382 4183 is-8 ta-383 sp-8 an-383 4184 is-8 ta-384 sp-8 an-384 4185 is-8 ta-385 sp-8 an-385 4186 is-8 ta-386 sp-8 an-386 4187 is-8 ta-387 sp-8 an-387 4188 is-8 ta-388 sp-8 an-388 4189 is-8 ta-389 sp-8 an-389 4190 is-8 ta-390 sp-8 an-390 4191 is-8 ta-391 sp-8 an-391 4192 is-8 ta-392 sp-8 an-392 4193 is-8 ta-393 sp-8 an-393 4194 is-9 ta-378 sp-9 an-378 4195 is-9 ta-379 sp-9 an-379 4196 is-9 ta-380 sp-9 an-380 4197 is-9 ta-381 sp-9 an-381 4198 is-9 ta-382 sp-9 an-382 4199 is-9 ta-383 sp-9 an-383 4200 is-9 ta-384 sp-9 an-384 4201 is-9 ta-385 sp-9 an-385 4202 is-9 ta-386 sp-9 an-386 4203 is-9 ta-387 sp-9 an-387 4204 is-9 ta-388 sp-9 an-388 4205 is-9 ta-389 sp-9 an-389 4206 is-9 ta-390 sp-9 an-390 4207 is-9 ta-391 sp-9 an-391 4208 is-9 ta-392 sp-9 an-392 4209 is-9 ta-393 sp-9 an-393 4210 is-14 ta-378 sp-14 an-378 4211 is-14 ta-379 sp-14 an-379 4212 is-14 ta-380 sp-14 an-380 4213 is-14 ta-381 sp-14 an-381 4214 is-14 ta-382 sp-14 an-382 4215 is-14 ta-383 sp-14 an-383 4216 is-14 ta-384 sp-14 an-384 4217 is-14 ta-385 sp-14 an-385 4218 is-14 ta-386 sp-14 an-386 4219 is-14 ta-387 sp-14 an-387 4220 is-14 ta-388 sp-14 an-388 4221 is-14 ta-389 sp-14 an-389 4222 is-14 ta-390 sp-14 an-390 4223 is-14 ta-391 sp-14 an-391 4224 is-14 ta-392 sp-14 an-392 4225 is-14 ta-393 sp-14 an-393 4226 is-15 ta-1 sp-23 an-1 4227 is-15 ta-2 sp-23 an-2 4228 is-15 ta-3 sp-23 an-3 4229 is-15 ta-4 sp-23 an-4 4230 is-15 ta-5 sp-23 an-5 4231 is-15 ta-6 sp-23 an-6 4232 is-15 ta-7 sp-23 an-7 4233 is-15 ta-8 sp-23 an-8 4234 is-15 ta-9 sp-23 an-9 4235 is-15 ta-10 sp-23 an-10 4236 is-15 ta-11 sp-23 an-11 4237 is-15 ta-12 sp-23 an-12 4238 is-15 ta-13 sp-23 an-13 4239 is-15 ta-14 sp-23 an-14 4240 is-15 ta-15 sp-23 an-15 4241 is-15 ta-16 sp-23 an-16 4242 is-15 ta-17 sp-23 an-17 4243 is-15 ta-18 sp-23 an-18 4244 is-15 ta-19 sp-23 an-19 4245 is-15 ta-20 sp-23 an-20 4246 is-15 ta-21 sp-23 an-21 4247 is-15 ta-22 sp-23 an-22 4248 is-15 ta-23 sp-23 an-23 4249 is-15 ta-24 sp-23 an-24 4250 is-15 ta-25 sp-23 an-25 4251 is-15 ta-26 sp-23 an-26 4252 is-15 ta-27 sp-23 an-27 4253 is-15 ta-28 sp-23 an-28 4254 is-15 ta-29 sp-23 an-29 4255 is-15 ta-30 sp-23 an-30 4256 is-15 ta-31 sp-23 an-31 4257 is-15 ta-32 sp-23 an-32 4258 is-15 ta-33 sp-23 an-33 4259 is-15 ta-34 sp-23 an-34 4260 is-15 ta-35 sp-23 an-35 4261 is-15 ta-36 sp-23 an-36 4262 is-15 ta-37 sp-23 an-37 4263 is-15 ta-38 sp-23 an-38 4264 is-15 ta-39 sp-23 an-39 4265 is-15 ta-40 sp-23 an-40 4266 is-15 ta-41 sp-23 an-41 4267 is-15 ta-42 sp-23 an-42 4268 is-15 ta-43 sp-23 an-43 4269 is-15 ta-44 sp-23 an-44 4270 is-15 ta-45 sp-23 an-45 4271 is-15 ta-46 sp-23 an-46 4272 is-15 ta-47 sp-23 an-47 4273 is-15 ta-48 sp-23 an-48 4274 is-15 ta-49 sp-23 an-49 4275 is-15 ta-50 sp-23 an-50 4276 is-15 ta-51 sp-23 an-51 4277 is-15 ta-52 sp-23 an-52 4278 is-15 ta-53 sp-23 an-53 4279 is-15 ta-54 sp-23 an-54 4280 is-15 ta-55 sp-23 an-55 4281 is-15 ta-56 sp-23 an-56 4282 is-15 ta-57 sp-23 an-57 4283 is-15 ta-58 sp-23 an-58 4284 is-15 ta-59 sp-23 an-59 4285 is-15 ta-60 sp-23 an-60 4286 is-15 ta-61 sp-23 an-61 4287 is-15 ta-62 sp-23 an-62 4288 is-15 ta-63 sp-23 an-63 4289 is-15 ta-64 sp-23 an-64 4290 is-15 ta-65 sp-23 an-65 4291 is-15 ta-66 sp-23 an-66 4292 is-15 ta-67 sp-23 an-67 4293 is-15 ta-68 sp-23 an-68 4294 is-15 ta-69 sp-23 an-69 4295 is-15 ta-70 sp-23 an-70 4296 is-15 ta-71 sp-23 an-71 4297 is-15 ta-72 sp-23 an-72 4298 is-15 ta-73 sp-23 an-73 4299 is-15 ta-74 sp-23 an-74 4300 is-15 ta-75 sp-23 an-75 4301 is-15 ta-76 sp-23 an-76 4302 is-15 ta-77 sp-23 an-77 4303 is-15 ta-78 sp-23 an-78 4304 is-15 ta-79 sp-23 an-79 4305 is-15 ta-80 sp-23 an-80 4306 is-15 ta-81 sp-23 an-81 4307 is-15 ta-82 sp-23 an-82 4308 is-15 ta-83 sp-23 an-83 4309 is-15 ta-84 sp-23 an-84 4310 is-15 ta-85 sp-23 an-85 4311 is-15 ta-86 sp-23 an-86 4312 is-15 ta-87 sp-23 an-87 4313 is-15 ta-88 sp-23 an-88 4314 is-15 ta-89 sp-23 an-89 4315 is-15 ta-90 sp-23 an-90 4316 is-15 ta-91 sp-23 an-91 4317 is-15 ta-92 sp-23 an-92 4318 is-15 ta-93 sp-23 an-93 4319 is-15 ta-94 sp-23 an-94 4320 is-15 ta-95 sp-23 an-95 4321 is-15 ta-96 sp-23 an-96 4322 is-15 ta-97 sp-23 an-97 4323 is-15 ta-98 sp-23 an-98 4324 is-15 ta-99 sp-23 an-99 4325 is-15 ta-100 sp-23 an-100 4326 is-15 ta-101 sp-23 an-101 4327 is-15 ta-102 sp-23 an-102 4328 is-15 ta-103 sp-23 an-103 4329 is-15 ta-104 sp-23 an-104 4330 is-15 ta-105 sp-23 an-105 4331 is-15 ta-106 sp-23 an-106 4332 is-15 ta-107 sp-23 an-107 4333 is-15 ta-108 sp-23 an-108 4334 is-15 ta-109 sp-23 an-109 4335 is-15 ta-110 sp-23 an-110 4336 is-15 ta-111 sp-23 an-111 4337 is-15 ta-112 sp-23 an-112 4338 is-15 ta-113 sp-23 an-113 4339 is-15 ta-114 sp-23 an-114 4340 is-15 ta-115 sp-23 an-115 4341 is-15 ta-116 sp-23 an-116 4342 is-15 ta-117 sp-23 an-117 4343 is-15 ta-118 sp-23 an-118 4344 is-15 ta-119 sp-23 an-119 4345 is-15 ta-120 sp-23 an-120 4346 is-15 ta-121 sp-23 an-121 4347 is-15 ta-122 sp-23 an-122 4348 is-15 ta-123 sp-23 an-123 4349 is-15 ta-124 sp-23 an-124 4350 is-15 ta-125 sp-23 an-125 4351 is-15 ta-126 sp-23 an-126 4352 is-15 ta-127 sp-23 an-127 4353 is-15 ta-128 sp-23 an-128 4354 is-15 ta-129 sp-23 an-129 4355 is-15 ta-130 sp-23 an-130 4356 is-15 ta-131 sp-23 an-131 4357 is-15 ta-132 sp-23 an-132 4358 is-15 ta-133 sp-23 an-133 4359 is-15 ta-134 sp-23 an-134 4360 is-15 ta-135 sp-23 an-135 4361 is-15 ta-136 sp-23 an-136 4362 is-15 ta-137 sp-23 an-137 4363 is-15 ta-138 sp-23 an-138 4364 is-15 ta-139 sp-23 an-139 4365 is-15 ta-140 sp-23 an-140 4366 is-15 ta-141 sp-23 an-141 4367 is-15 ta-142 sp-23 an-142 4368 is-15 ta-143 sp-23 an-143 4369 is-15 ta-144 sp-23 an-144 4370 is-15 ta-145 sp-23 an-145 4371 is-15 ta-146 sp-23 an-146 4372 is-15 ta-147 sp-23 an-147 4373 is-15 ta-148 sp-23 an-148 4374 is-15 ta-149 sp-23 an-149 4375 is-15 ta-150 sp-23 an-150 4376 is-15 ta-151 sp-23 an-151 4377 is-15 ta-152 sp-23 an-152 4378 is-15 ta-153 sp-23 an-153 4379 is-15 ta-154 sp-23 an-154 4380 is-15 ta-155 sp-23 an-155 4381 is-15 ta-156 sp-23 an-156 4382 is-15 ta-157 sp-23 an-157 4383 is-15 ta-158 sp-23 an-158 4384 is-15 ta-159 sp-23 an-159 4385 is-15 ta-160 sp-23 an-160 4386 is-15 ta-161 sp-23 an-161 4387 is-15 ta-162 sp-23 an-162 4388 is-15 ta-163 sp-23 an-163 4389 is-15 ta-164 sp-23 an-164 4390 is-15 ta-165 sp-23 an-165 4391 is-15 ta-166 sp-23 an-166 4392 is-15 ta-167 sp-23 an-167 4393 is-15 ta-168 sp-23 an-168 4394 is-15 ta-169 sp-23 an-169 4395 is-15 ta-170 sp-23 an-170 4396 is-15 ta-171 sp-23 an-171 4397 is-15 ta-172 sp-23 an-172 4398 is-15 ta-173 sp-23 an-173 4399 is-15 ta-174 sp-23 an-174 4400 is-15 ta-175 sp-23 an-175 4401 is-15 ta-176 sp-23 an-176 4402 is-15 ta-177 sp-23 an-177 4403 is-15 ta-178 sp-23 an-178 4404 is-15 ta-179 sp-23 an-179 4405 is-15 ta-180 sp-23 an-180 4406 is-15 ta-181 sp-23 an-181 4407 is-15 ta-182 sp-23 an-182 4408 is-15 ta-183 sp-23 an-183 4409 is-15 ta-184 sp-23 an-184 4410 is-15 ta-185 sp-23 an-185 4411 is-15 ta-186 sp-23 an-186 4412 is-15 ta-187 sp-23 an-187 4413 is-15 ta-188 sp-23 an-188 4414 is-15 ta-189 sp-23 an-189 4415 is-15 ta-190 sp-23 an-190 4416 is-15 ta-191 sp-23 an-191 4417 is-15 ta-192 sp-23 an-192 4418 is-15 ta-193 sp-23 an-193 4419 is-15 ta-194 sp-23 an-194 4420 is-15 ta-195 sp-23 an-195 4421 is-15 ta-196 sp-23 an-196 4422 is-15 ta-197 sp-23 an-197 4423 is-15 ta-198 sp-23 an-198 4424 is-15 ta-199 sp-23 an-199 4425 is-15 ta-200 sp-23 an-200 4426 is-15 ta-201 sp-23 an-201 4427 is-15 ta-202 sp-23 an-202 4428 is-15 ta-203 sp-23 an-203 4429 is-15 ta-204 sp-23 an-204 4430 is-15 ta-205 sp-23 an-205 4431 is-15 ta-206 sp-23 an-206 4432 is-15 ta-207 sp-23 an-207 4433 is-15 ta-208 sp-23 an-208 4434 is-15 ta-209 sp-23 an-209 4435 is-15 ta-210 sp-23 an-210 4436 is-15 ta-211 sp-23 an-211 4437 is-15 ta-212 sp-23 an-212 4438 is-15 ta-213 sp-23 an-213 4439 is-15 ta-214 sp-23 an-214 4440 is-15 ta-215 sp-23 an-215 4441 is-15 ta-216 sp-23 an-216 4442 is-15 ta-217 sp-23 an-217 4443 is-15 ta-218 sp-23 an-218 4444 is-15 ta-219 sp-23 an-219 4445 is-15 ta-220 sp-23 an-220 4446 is-15 ta-221 sp-23 an-221 4447 is-15 ta-222 sp-23 an-222 4448 is-15 ta-223 sp-23 an-223 4449 is-15 ta-224 sp-23 an-224 4450 is-15 ta-225 sp-23 an-225 4451 is-15 ta-226 sp-23 an-226 4452 is-15 ta-227 sp-23 an-227 4453 is-15 ta-228 sp-23 an-228 4454 is-15 ta-229 sp-23 an-229 4455 is-15 ta-230 sp-23 an-230 4456 is-15 ta-231 sp-23 an-231 4457 is-15 ta-232 sp-23 an-232 4458 is-15 ta-233 sp-23 an-233 4459 is-15 ta-234 sp-23 an-234 4460 is-15 ta-235 sp-23 an-235 4461 is-15 ta-236 sp-23 an-236 4462 is-15 ta-237 sp-23 an-237 4463 is-15 ta-238 sp-23 an-238 4464 is-15 ta-239 sp-23 an-239 4465 is-15 ta-240 sp-23 an-240 4466 is-15 ta-241 sp-23 an-241 4467 is-15 ta-242 sp-23 an-242 4468 is-15 ta-243 sp-23 an-243 4469 is-15 ta-244 sp-23 an-244 4470 is-15 ta-245 sp-23 an-245 4471 is-15 ta-246 sp-23 an-246 4472 is-15 ta-247 sp-23 an-247 4473 is-15 ta-248 sp-23 an-248 4474 is-15 ta-249 sp-23 an-249 4475 is-15 ta-250 sp-23 an-250 4476 is-15 ta-251 sp-23 an-251 4477 is-15 ta-252 sp-23 an-252 4478 is-15 ta-253 sp-23 an-253 4479 is-15 ta-254 sp-23 an-254 4480 is-15 ta-255 sp-23 an-255 4481 is-15 ta-256 sp-23 an-256 4482 is-15 ta-257 sp-23 an-257 4483 is-15 ta-258 sp-23 an-258 4484 is-15 ta-259 sp-23 an-259 4485 is-15 ta-260 sp-23 an-260 4486 is-15 ta-261 sp-23 an-261 4487 is-15 ta-262 sp-23 an-262 4488 is-15 ta-263 sp-23 an-263 4489 is-15 ta-264 sp-23 an-264 4490 is-15 ta-265 sp-23 an-265 4491 is-15 ta-266 sp-23 an-266 4492 is-15 ta-267 sp-23 an-267 4493 is-15 ta-268 sp-23 an-268 4494 is-15 ta-269 sp-23 an-269 4495 is-15 ta-270 sp-23 an-270 4496 is-15 ta-271 sp-23 an-271 4497 is-15 ta-272 sp-23 an-272 4498 is-15 ta-273 sp-23 an-273 4499 is-15 ta-274 sp-23 an-274 4500 is-15 ta-275 sp-23 an-275 4501 is-15 ta-276 sp-23 an-276 4502 is-15 ta-277 sp-23 an-277 4503 is-15 ta-278 sp-23 an-278 4504 is-15 ta-279 sp-23 an-279 4505 is-15 ta-280 sp-23 an-280 4506 is-15 ta-281 sp-23 an-281 4507 is-15 ta-282 sp-23 an-282 4508 is-15 ta-283 sp-23 an-283 4509 is-15 ta-284 sp-23 an-284 4510 is-15 ta-285 sp-23 an-285 4511 is-15 ta-286 sp-23 an-286 4512 is-15 ta-287 sp-23 an-287 4513 is-15 ta-288 sp-23 an-288 4514 is-15 ta-289 sp-23 an-289 4515 is-15 ta-290 sp-23 an-290 4516 is-15 ta-291 sp-23 an-291 4517 is-15 ta-292 sp-23 an-292 4518 is-15 ta-293 sp-23 an-293 4519 is-15 ta-294 sp-23 an-294 4520 is-15 ta-295 sp-23 an-295 4521 is-15 ta-296 sp-23 an-296 4522 is-15 ta-297 sp-23 an-297 4523 is-15 ta-298 sp-23 an-298 4524 is-15 ta-299 sp-23 an-299 4525 is-15 ta-300 sp-23 an-300 4526 is-15 ta-301 sp-23 an-301 4527 is-15 ta-302 sp-23 an-302 4528 is-15 ta-303 sp-23 an-303 4529 is-15 ta-304 sp-23 an-304 4530 is-15 ta-305 sp-23 an-305 4531 is-15 ta-306 sp-23 an-306 4532 is-15 ta-307 sp-23 an-307 4533 is-15 ta-308 sp-23 an-308 4534 is-15 ta-309 sp-23 an-309 4535 is-15 ta-310 sp-23 an-310 4536 is-15 ta-311 sp-23 an-311 4537 is-15 ta-312 sp-23 an-312 4538 is-15 ta-313 sp-23 an-313 4539 is-15 ta-314 sp-23 an-314 4540 is-15 ta-315 sp-23 an-315 4541 is-15 ta-316 sp-23 an-316 4542 is-15 ta-317 sp-23 an-317 4543 is-15 ta-318 sp-23 an-318 4544 is-15 ta-319 sp-23 an-319 4545 is-15 ta-320 sp-23 an-320 4546 is-15 ta-321 sp-23 an-321 4547 is-15 ta-322 sp-23 an-322 4548 is-15 ta-323 sp-23 an-323 4549 is-15 ta-324 sp-23 an-324 4550 is-15 ta-325 sp-23 an-325 4551 is-15 ta-326 sp-23 an-326 4552 is-15 ta-327 sp-23 an-327 4553 is-15 ta-328 sp-23 an-328 4554 is-15 ta-329 sp-23 an-329 4555 is-15 ta-330 sp-23 an-330 4556 is-15 ta-331 sp-23 an-331 4557 is-15 ta-332 sp-23 an-332 4558 is-15 ta-333 sp-23 an-333 4559 is-15 ta-334 sp-23 an-334 4560 is-15 ta-335 sp-23 an-335 4561 is-15 ta-336 sp-23 an-336 4562 is-15 ta-337 sp-23 an-337 4563 is-15 ta-338 sp-23 an-338 4564 is-15 ta-339 sp-23 an-339 4565 is-15 ta-340 sp-23 an-340 4566 is-15 ta-341 sp-23 an-341 4567 is-15 ta-342 sp-23 an-342 4568 is-15 ta-343 sp-23 an-343 4569 is-15 ta-344 sp-23 an-344 4570 is-15 ta-345 sp-23 an-345 4571 is-15 ta-346 sp-23 an-346 4572 is-15 ta-347 sp-23 an-347 4573 is-15 ta-348 sp-23 an-348 4574 is-15 ta-349 sp-23 an-349 4575 is-15 ta-350 sp-23 an-350 4576 is-15 ta-351 sp-23 an-351 4577 is-15 ta-352 sp-23 an-352 4578 is-15 ta-353 sp-23 an-353 4579 is-15 ta-354 sp-23 an-354 4580 is-15 ta-355 sp-23 an-355 4581 is-15 ta-356 sp-23 an-356 4582 is-15 ta-357 sp-23 an-357 4583 is-15 ta-358 sp-23 an-358 4584 is-15 ta-359 sp-23 an-359 4585 is-15 ta-360 sp-23 an-360 4586 is-15 ta-361 sp-23 an-361 4587 is-15 ta-362 sp-23 an-362 4588 is-15 ta-363 sp-23 an-363 4589 is-15 ta-364 sp-23 an-364 4590 is-15 ta-365 sp-23 an-365 4591 is-15 ta-366 sp-23 an-366 4592 is-15 ta-367 sp-23 an-367 4593 is-15 ta-368 sp-23 an-368 4594 is-15 ta-369 sp-23 an-369 4595 is-15 ta-370 sp-23 an-370 4596 is-15 ta-371 sp-23 an-371 4597 is-15 ta-372 sp-23 an-372 4598 is-15 ta-373 sp-23 an-373 4599 is-15 ta-374 sp-23 an-374 4600 is-15 ta-375 sp-23 an-375 4601 is-15 ta-376 sp-23 an-376 4602 is-15 ta-377 sp-23 an-377 4603 is-15 ta-378 sp-23 an-378 4604 is-15 ta-379 sp-23 an-379 4605 is-15 ta-380 sp-23 an-380 4606 is-15 ta-381 sp-23 an-381 4607 is-15 ta-382 sp-23 an-382 4608 is-15 ta-383 sp-23 an-383 4609 is-15 ta-384 sp-23 an-384 4610 is-15 ta-385 sp-23 an-385 4611 is-15 ta-386 sp-23 an-386 4612 is-15 ta-387 sp-23 an-387 4613 is-15 ta-388 sp-23 an-388 4614 is-15 ta-389 sp-23 an-389 4615 is-15 ta-390 sp-23 an-390 4616 is-15 ta-391 sp-23 an-391 4617 is-15 ta-392 sp-23 an-392 4618 is-15 ta-393 sp-23 an-393 4619 is-16 ta-1 sp-24 an-1 4620 is-16 ta-2 sp-24 an-2 4621 is-16 ta-3 sp-24 an-3 4622 is-16 ta-4 sp-24 an-4 4623 is-16 ta-5 sp-24 an-5 4624 is-16 ta-6 sp-24 an-6 4625 is-16 ta-7 sp-24 an-7 4626 is-16 ta-8 sp-24 an-8 4627 is-16 ta-9 sp-24 an-9 4628 is-16 ta-10 sp-24 an-10 4629 is-16 ta-11 sp-24 an-11 4630 is-16 ta-12 sp-24 an-12 4631 is-16 ta-13 sp-24 an-13 4632 is-16 ta-14 sp-24 an-14 4633 is-16 ta-15 sp-24 an-15 4634 is-16 ta-16 sp-24 an-16 4635 is-16 ta-17 sp-24 an-17 4636 is-16 ta-18 sp-24 an-18 4637 is-16 ta-19 sp-24 an-19 4638 is-16 ta-20 sp-24 an-20 4639 is-16 ta-21 sp-24 an-21 4640 is-16 ta-22 sp-24 an-22 4641 is-16 ta-23 sp-24 an-23 4642 is-16 ta-24 sp-24 an-24 4643 is-16 ta-25 sp-24 an-25 4644 is-16 ta-26 sp-24 an-26 4645 is-16 ta-27 sp-24 an-27 4646 is-16 ta-28 sp-24 an-28 4647 is-16 ta-29 sp-24 an-29 4648 is-16 ta-30 sp-24 an-30 4649 is-16 ta-31 sp-24 an-31 4650 is-16 ta-32 sp-24 an-32 4651 is-16 ta-33 sp-24 an-33 4652 is-16 ta-34 sp-24 an-34 4653 is-16 ta-35 sp-24 an-35 4654 is-16 ta-36 sp-24 an-36 4655 is-16 ta-37 sp-24 an-37 4656 is-16 ta-38 sp-24 an-38 4657 is-16 ta-39 sp-24 an-39 4658 is-16 ta-40 sp-24 an-40 4659 is-16 ta-41 sp-24 an-41 4660 is-16 ta-42 sp-24 an-42 4661 is-16 ta-43 sp-24 an-43 4662 is-16 ta-44 sp-24 an-44 4663 is-16 ta-45 sp-24 an-45 4664 is-16 ta-46 sp-24 an-46 4665 is-16 ta-47 sp-24 an-47 4666 is-16 ta-48 sp-24 an-48 4667 is-16 ta-49 sp-24 an-49 4668 is-16 ta-50 sp-24 an-50 4669 is-16 ta-51 sp-24 an-51 4670 is-16 ta-52 sp-24 an-52 4671 is-16 ta-53 sp-24 an-53 4672 is-16 ta-54 sp-24 an-54 4673 is-16 ta-55 sp-24 an-55 4674 is-16 ta-56 sp-24 an-56 4675 is-16 ta-57 sp-24 an-57 4676 is-16 ta-58 sp-24 an-58 4677 is-16 ta-59 sp-24 an-59 4678 is-16 ta-60 sp-24 an-60 4679 is-16 ta-61 sp-24 an-61 4680 is-16 ta-62 sp-24 an-62 4681 is-16 ta-63 sp-24 an-63 4682 is-16 ta-64 sp-24 an-64 4683 is-16 ta-65 sp-24 an-65 4684 is-16 ta-66 sp-24 an-66 4685 is-16 ta-67 sp-24 an-67 4686 is-16 ta-68 sp-24 an-68 4687 is-16 ta-69 sp-24 an-69 4688 is-16 ta-70 sp-24 an-70 4689 is-16 ta-71 sp-24 an-71 4690 is-16 ta-72 sp-24 an-72 4691 is-16 ta-73 sp-24 an-73 4692 is-16 ta-74 sp-24 an-74 4693 is-16 ta-75 sp-24 an-75 4694 is-16 ta-76 sp-24 an-76 4695 is-16 ta-77 sp-24 an-77 4696 is-16 ta-78 sp-24 an-78 4697 is-16 ta-79 sp-24 an-79 4698 is-16 ta-80 sp-24 an-80 4699 is-16 ta-81 sp-24 an-81 4700 is-16 ta-82 sp-24 an-82 4701 is-16 ta-83 sp-24 an-83 4702 is-16 ta-84 sp-24 an-84 4703 is-16 ta-85 sp-24 an-85 4704 is-16 ta-86 sp-24 an-86 4705 is-16 ta-87 sp-24 an-87 4706 is-16 ta-88 sp-24 an-88 4707 is-16 ta-89 sp-24 an-89 4708 is-16 ta-90 sp-24 an-90 4709 is-16 ta-91 sp-24 an-91 4710 is-16 ta-92 sp-24 an-92 4711 is-16 ta-93 sp-24 an-93 4712 is-16 ta-94 sp-24 an-94 4713 is-16 ta-95 sp-24 an-95 4714 is-16 ta-96 sp-24 an-96 4715 is-16 ta-97 sp-24 an-97 4716 is-16 ta-98 sp-24 an-98 4717 is-16 ta-99 sp-24 an-99 4718 is-16 ta-100 sp-24 an-100 4719 is-16 ta-101 sp-24 an-101 4720 is-16 ta-102 sp-24 an-102 4721 is-16 ta-103 sp-24 an-103 4722 is-16 ta-104 sp-24 an-104 4723 is-16 ta-105 sp-24 an-105 4724 is-16 ta-106 sp-24 an-106 4725 is-16 ta-107 sp-24 an-107 4726 is-16 ta-108 sp-24 an-108 4727 is-16 ta-109 sp-24 an-109 4728 is-16 ta-110 sp-24 an-110 4729 is-16 ta-111 sp-24 an-111 4730 is-16 ta-112 sp-24 an-112 4731 is-16 ta-113 sp-24 an-113 4732 is-16 ta-114 sp-24 an-114 4733 is-16 ta-115 sp-24 an-115 4734 is-16 ta-116 sp-24 an-116 4735 is-16 ta-117 sp-24 an-117 4736 is-16 ta-118 sp-24 an-118 4737 is-16 ta-119 sp-24 an-119 4738 is-16 ta-120 sp-24 an-120 4739 is-16 ta-121 sp-24 an-121 4740 is-16 ta-122 sp-24 an-122 4741 is-16 ta-123 sp-24 an-123 4742 is-16 ta-124 sp-24 an-124 4743 is-16 ta-125 sp-24 an-125 4744 is-16 ta-126 sp-24 an-126 4745 is-16 ta-127 sp-24 an-127 4746 is-16 ta-128 sp-24 an-128 4747 is-16 ta-129 sp-24 an-129 4748 is-16 ta-130 sp-24 an-130 4749 is-16 ta-131 sp-24 an-131 4750 is-16 ta-132 sp-24 an-132 4751 is-16 ta-133 sp-24 an-133 4752 is-16 ta-134 sp-24 an-134 4753 is-16 ta-135 sp-24 an-135 4754 is-16 ta-136 sp-24 an-136 4755 is-16 ta-137 sp-24 an-137 4756 is-16 ta-138 sp-24 an-138 4757 is-16 ta-139 sp-24 an-139 4758 is-16 ta-140 sp-24 an-140 4759 is-16 ta-141 sp-24 an-141 4760 is-16 ta-142 sp-24 an-142 4761 is-16 ta-143 sp-24 an-143 4762 is-16 ta-144 sp-24 an-144 4763 is-16 ta-145 sp-24 an-145 4764 is-16 ta-146 sp-24 an-146 4765 is-16 ta-147 sp-24 an-147 4766 is-16 ta-148 sp-24 an-148 4767 is-16 ta-149 sp-24 an-149 4768 is-16 ta-150 sp-24 an-150 4769 is-16 ta-151 sp-24 an-151 4770 is-16 ta-152 sp-24 an-152 4771 is-16 ta-153 sp-24 an-153 4772 is-16 ta-154 sp-24 an-154 4773 is-16 ta-155 sp-24 an-155 4774 is-16 ta-156 sp-24 an-156 4775 is-16 ta-157 sp-24 an-157 4776 is-16 ta-158 sp-24 an-158 4777 is-16 ta-159 sp-24 an-159 4778 is-16 ta-160 sp-24 an-160 4779 is-16 ta-161 sp-24 an-161 4780 is-16 ta-162 sp-24 an-162 4781 is-16 ta-163 sp-24 an-163 4782 is-16 ta-164 sp-24 an-164 4783 is-16 ta-165 sp-24 an-165 4784 is-16 ta-166 sp-24 an-166 4785 is-16 ta-167 sp-24 an-167 4786 is-16 ta-168 sp-24 an-168 4787 is-16 ta-169 sp-24 an-169 4788 is-16 ta-170 sp-24 an-170 4789 is-16 ta-171 sp-24 an-171 4790 is-16 ta-172 sp-24 an-172 4791 is-16 ta-173 sp-24 an-173 4792 is-16 ta-174 sp-24 an-174 4793 is-16 ta-175 sp-24 an-175 4794 is-16 ta-176 sp-24 an-176 4795 is-16 ta-177 sp-24 an-177 4796 is-16 ta-178 sp-24 an-178 4797 is-16 ta-179 sp-24 an-179 4798 is-16 ta-180 sp-24 an-180 4799 is-16 ta-181 sp-24 an-181 4800 is-16 ta-182 sp-24 an-182 4801 is-16 ta-183 sp-24 an-183 4802 is-16 ta-184 sp-24 an-184 4803 is-16 ta-185 sp-24 an-185 4804 is-16 ta-186 sp-24 an-186 4805 is-16 ta-187 sp-24 an-187 4806 is-16 ta-188 sp-24 an-188 4807 is-16 ta-189 sp-24 an-189 4808 is-16 ta-190 sp-24 an-190 4809 is-16 ta-191 sp-24 an-191 4810 is-16 ta-192 sp-24 an-192 4811 is-16 ta-193 sp-24 an-193 4812 is-16 ta-194 sp-24 an-194 4813 is-16 ta-195 sp-24 an-195 4814 is-16 ta-196 sp-24 an-196 4815 is-16 ta-197 sp-24 an-197 4816 is-16 ta-198 sp-24 an-198 4817 is-16 ta-199 sp-24 an-199 4818 is-16 ta-200 sp-24 an-200 4819 is-16 ta-201 sp-24 an-201 4820 is-16 ta-202 sp-24 an-202 4821 is-16 ta-203 sp-24 an-203 4822 is-16 ta-204 sp-24 an-204 4823 is-16 ta-205 sp-24 an-205 4824 is-16 ta-206 sp-24 an-206 4825 is-16 ta-207 sp-24 an-207 4826 is-16 ta-208 sp-24 an-208 4827 is-16 ta-209 sp-24 an-209 4828 is-16 ta-210 sp-24 an-210 4829 is-16 ta-211 sp-24 an-211 4830 is-16 ta-212 sp-24 an-212 4831 is-16 ta-213 sp-24 an-213 4832 is-16 ta-214 sp-24 an-214 4833 is-16 ta-215 sp-24 an-215 4834 is-16 ta-216 sp-24 an-216 4835 is-16 ta-217 sp-24 an-217 4836 is-16 ta-218 sp-24 an-218 4837 is-16 ta-219 sp-24 an-219 4838 is-16 ta-220 sp-24 an-220 4839 is-16 ta-221 sp-24 an-221 4840 is-16 ta-222 sp-24 an-222 4841 is-16 ta-223 sp-24 an-223 4842 is-16 ta-224 sp-24 an-224 4843 is-16 ta-225 sp-24 an-225 4844 is-16 ta-226 sp-24 an-226 4845 is-16 ta-227 sp-24 an-227 4846 is-16 ta-228 sp-24 an-228 4847 is-16 ta-229 sp-24 an-229 4848 is-16 ta-230 sp-24 an-230 4849 is-16 ta-231 sp-24 an-231 4850 is-16 ta-232 sp-24 an-232 4851 is-16 ta-233 sp-24 an-233 4852 is-16 ta-234 sp-24 an-234 4853 is-16 ta-235 sp-24 an-235 4854 is-16 ta-236 sp-24 an-236 4855 is-16 ta-237 sp-24 an-237 4856 is-16 ta-238 sp-24 an-238 4857 is-16 ta-239 sp-24 an-239 4858 is-16 ta-240 sp-24 an-240 4859 is-16 ta-241 sp-24 an-241 4860 is-16 ta-242 sp-24 an-242 4861 is-16 ta-243 sp-24 an-243 4862 is-16 ta-244 sp-24 an-244 4863 is-16 ta-245 sp-24 an-245 4864 is-16 ta-246 sp-24 an-246 4865 is-16 ta-247 sp-24 an-247 4866 is-16 ta-248 sp-24 an-248 4867 is-16 ta-249 sp-24 an-249 4868 is-16 ta-250 sp-24 an-250 4869 is-16 ta-251 sp-24 an-251 4870 is-16 ta-252 sp-24 an-252 4871 is-16 ta-253 sp-24 an-253 4872 is-16 ta-254 sp-24 an-254 4873 is-16 ta-255 sp-24 an-255 4874 is-16 ta-256 sp-24 an-256 4875 is-16 ta-257 sp-24 an-257 4876 is-16 ta-258 sp-24 an-258 4877 is-16 ta-259 sp-24 an-259 4878 is-16 ta-260 sp-24 an-260 4879 is-16 ta-261 sp-24 an-261 4880 is-16 ta-262 sp-24 an-262 4881 is-16 ta-263 sp-24 an-263 4882 is-16 ta-264 sp-24 an-264 4883 is-16 ta-265 sp-24 an-265 4884 is-16 ta-266 sp-24 an-266 4885 is-16 ta-267 sp-24 an-267 4886 is-16 ta-268 sp-24 an-268 4887 is-16 ta-269 sp-24 an-269 4888 is-16 ta-270 sp-24 an-270 4889 is-16 ta-271 sp-24 an-271 4890 is-16 ta-272 sp-24 an-272 4891 is-16 ta-273 sp-24 an-273 4892 is-16 ta-274 sp-24 an-274 4893 is-16 ta-275 sp-24 an-275 4894 is-16 ta-276 sp-24 an-276 4895 is-16 ta-277 sp-24 an-277 4896 is-16 ta-278 sp-24 an-278 4897 is-16 ta-279 sp-24 an-279 4898 is-16 ta-280 sp-24 an-280 4899 is-16 ta-281 sp-24 an-281 4900 is-16 ta-282 sp-24 an-282 4901 is-16 ta-283 sp-24 an-283 4902 is-16 ta-284 sp-24 an-284 4903 is-16 ta-285 sp-24 an-285 4904 is-16 ta-286 sp-24 an-286 4905 is-16 ta-287 sp-24 an-287 4906 is-16 ta-288 sp-24 an-288 4907 is-16 ta-289 sp-24 an-289 4908 is-16 ta-290 sp-24 an-290 4909 is-16 ta-291 sp-24 an-291 4910 is-16 ta-292 sp-24 an-292 4911 is-16 ta-293 sp-24 an-293 4912 is-16 ta-294 sp-24 an-294 4913 is-16 ta-295 sp-24 an-295 4914 is-16 ta-296 sp-24 an-296 4915 is-16 ta-297 sp-24 an-297 4916 is-16 ta-298 sp-24 an-298 4917 is-16 ta-299 sp-24 an-299 4918 is-16 ta-300 sp-24 an-300 4919 is-16 ta-301 sp-24 an-301 4920 is-16 ta-302 sp-24 an-302 4921 is-16 ta-303 sp-24 an-303 4922 is-16 ta-304 sp-24 an-304 4923 is-16 ta-305 sp-24 an-305 4924 is-16 ta-306 sp-24 an-306 4925 is-16 ta-307 sp-24 an-307 4926 is-16 ta-308 sp-24 an-308 4927 is-16 ta-309 sp-24 an-309 4928 is-16 ta-310 sp-24 an-310 4929 is-16 ta-311 sp-24 an-311 4930 is-16 ta-312 sp-24 an-312 4931 is-16 ta-313 sp-24 an-313 4932 is-16 ta-314 sp-24 an-314 4933 is-16 ta-315 sp-24 an-315 4934 is-16 ta-316 sp-24 an-316 4935 is-16 ta-317 sp-24 an-317 4936 is-16 ta-318 sp-24 an-318 4937 is-16 ta-319 sp-24 an-319 4938 is-16 ta-320 sp-24 an-320 4939 is-16 ta-321 sp-24 an-321 4940 is-16 ta-322 sp-24 an-322 4941 is-16 ta-323 sp-24 an-323 4942 is-16 ta-324 sp-24 an-324 4943 is-16 ta-325 sp-24 an-325 4944 is-16 ta-326 sp-24 an-326 4945 is-16 ta-327 sp-24 an-327 4946 is-16 ta-328 sp-24 an-328 4947 is-16 ta-329 sp-24 an-329 4948 is-16 ta-330 sp-24 an-330 4949 is-16 ta-331 sp-24 an-331 4950 is-16 ta-332 sp-24 an-332 4951 is-16 ta-333 sp-24 an-333 4952 is-16 ta-334 sp-24 an-334 4953 is-16 ta-335 sp-24 an-335 4954 is-16 ta-336 sp-24 an-336 4955 is-16 ta-337 sp-24 an-337 4956 is-16 ta-338 sp-24 an-338 4957 is-16 ta-339 sp-24 an-339 4958 is-16 ta-340 sp-24 an-340 4959 is-16 ta-341 sp-24 an-341 4960 is-16 ta-342 sp-24 an-342 4961 is-16 ta-343 sp-24 an-343 4962 is-16 ta-344 sp-24 an-344 4963 is-16 ta-345 sp-24 an-345 4964 is-16 ta-346 sp-24 an-346 4965 is-16 ta-347 sp-24 an-347 4966 is-16 ta-348 sp-24 an-348 4967 is-16 ta-349 sp-24 an-349 4968 is-16 ta-350 sp-24 an-350 4969 is-16 ta-351 sp-24 an-351 4970 is-16 ta-352 sp-24 an-352 4971 is-16 ta-353 sp-24 an-353 4972 is-16 ta-354 sp-24 an-354 4973 is-16 ta-355 sp-24 an-355 4974 is-16 ta-356 sp-24 an-356 4975 is-16 ta-357 sp-24 an-357 4976 is-16 ta-358 sp-24 an-358 4977 is-16 ta-359 sp-24 an-359 4978 is-16 ta-360 sp-24 an-360 4979 is-16 ta-361 sp-24 an-361 4980 is-16 ta-362 sp-24 an-362 4981 is-16 ta-363 sp-24 an-363 4982 is-16 ta-364 sp-24 an-364 4983 is-16 ta-365 sp-24 an-365 4984 is-16 ta-366 sp-24 an-366 4985 is-16 ta-367 sp-24 an-367 4986 is-16 ta-368 sp-24 an-368 4987 is-16 ta-369 sp-24 an-369 4988 is-16 ta-370 sp-24 an-370 4989 is-16 ta-371 sp-24 an-371 4990 is-16 ta-372 sp-24 an-372 4991 is-16 ta-373 sp-24 an-373 4992 is-16 ta-374 sp-24 an-374 4993 is-16 ta-375 sp-24 an-375 4994 is-16 ta-376 sp-24 an-376 4995 is-16 ta-377 sp-24 an-377 4996 is-16 ta-378 sp-24 an-378 4997 is-16 ta-379 sp-24 an-379 4998 is-16 ta-380 sp-24 an-380 4999 is-16 ta-381 sp-24 an-381 5000 is-16 ta-382 sp-24 an-382 5001 is-16 ta-383 sp-24 an-383 5002 is-16 ta-384 sp-24 an-384 5003 is-16 ta-385 sp-24 an-385 5004 is-16 ta-386 sp-24 an-386 5005 is-16 ta-387 sp-24 an-387 5006 is-16 ta-388 sp-24 an-388 5007 is-16 ta-389 sp-24 an-389 5008 is-16 ta-390 sp-24 an-390 5009 is-16 ta-391 sp-24 an-391 5010 is-16 ta-392 sp-24 an-392 5011 is-16 ta-393 sp-24 an-393 5012 is-17 ta-1 sp-25 an-1 5013 is-17 ta-2 sp-25 an-2 5014 is-17 ta-3 sp-25 an-3 5015 is-17 ta-4 sp-25 an-4 5016 is-17 ta-5 sp-25 an-5 5017 is-17 ta-6 sp-25 an-6 5018 is-17 ta-7 sp-25 an-7 5019 is-17 ta-8 sp-25 an-8 5020 is-17 ta-9 sp-25 an-9 5021 is-17 ta-10 sp-25 an-10 5022 is-17 ta-11 sp-25 an-11 5023 is-17 ta-12 sp-25 an-12 5024 is-17 ta-13 sp-25 an-13 5025 is-17 ta-14 sp-25 an-14 5026 is-17 ta-15 sp-25 an-15 5027 is-17 ta-16 sp-25 an-16 5028 is-17 ta-17 sp-25 an-17 5029 is-17 ta-18 sp-25 an-18 5030 is-17 ta-19 sp-25 an-19 5031 is-17 ta-20 sp-25 an-20 5032 is-17 ta-21 sp-25 an-21 5033 is-17 ta-22 sp-25 an-22 5034 is-17 ta-23 sp-25 an-23 5035 is-17 ta-24 sp-25 an-24 5036 is-17 ta-25 sp-25 an-25 5037 is-17 ta-26 sp-25 an-26 5038 is-17 ta-27 sp-25 an-27 5039 is-17 ta-28 sp-25 an-28 5040 is-17 ta-29 sp-25 an-29 5041 is-17 ta-30 sp-25 an-30 5042 is-17 ta-31 sp-25 an-31 5043 is-17 ta-32 sp-25 an-32 5044 is-17 ta-33 sp-25 an-33 5045 is-17 ta-34 sp-25 an-34 5046 is-17 ta-35 sp-25 an-35 5047 is-17 ta-36 sp-25 an-36 5048 is-17 ta-37 sp-25 an-37 5049 is-17 ta-38 sp-25 an-38 5050 is-17 ta-39 sp-25 an-39 5051 is-17 ta-40 sp-25 an-40 5052 is-17 ta-41 sp-25 an-41 5053 is-17 ta-42 sp-25 an-42 5054 is-17 ta-43 sp-25 an-43 5055 is-17 ta-44 sp-25 an-44 5056 is-17 ta-45 sp-25 an-45 5057 is-17 ta-46 sp-25 an-46 5058 is-17 ta-47 sp-25 an-47 5059 is-17 ta-48 sp-25 an-48 5060 is-17 ta-49 sp-25 an-49 5061 is-17 ta-50 sp-25 an-50 5062 is-17 ta-51 sp-25 an-51 5063 is-17 ta-52 sp-25 an-52 5064 is-17 ta-53 sp-25 an-53 5065 is-17 ta-54 sp-25 an-54 5066 is-17 ta-55 sp-25 an-55 5067 is-17 ta-56 sp-25 an-56 5068 is-17 ta-57 sp-25 an-57 5069 is-17 ta-58 sp-25 an-58 5070 is-17 ta-59 sp-25 an-59 5071 is-17 ta-60 sp-25 an-60 5072 is-17 ta-61 sp-25 an-61 5073 is-17 ta-62 sp-25 an-62 5074 is-17 ta-63 sp-25 an-63 5075 is-17 ta-64 sp-25 an-64 5076 is-17 ta-65 sp-25 an-65 5077 is-17 ta-66 sp-25 an-66 5078 is-17 ta-67 sp-25 an-67 5079 is-17 ta-68 sp-25 an-68 5080 is-17 ta-69 sp-25 an-69 5081 is-17 ta-70 sp-25 an-70 5082 is-17 ta-71 sp-25 an-71 5083 is-17 ta-72 sp-25 an-72 5084 is-17 ta-73 sp-25 an-73 5085 is-17 ta-74 sp-25 an-74 5086 is-17 ta-75 sp-25 an-75 5087 is-17 ta-76 sp-25 an-76 5088 is-17 ta-77 sp-25 an-77 5089 is-17 ta-78 sp-25 an-78 5090 is-17 ta-79 sp-25 an-79 5091 is-17 ta-80 sp-25 an-80 5092 is-17 ta-81 sp-25 an-81 5093 is-17 ta-82 sp-25 an-82 5094 is-17 ta-83 sp-25 an-83 5095 is-17 ta-84 sp-25 an-84 5096 is-17 ta-85 sp-25 an-85 5097 is-17 ta-86 sp-25 an-86 5098 is-17 ta-87 sp-25 an-87 5099 is-17 ta-88 sp-25 an-88 5100 is-17 ta-89 sp-25 an-89 5101 is-17 ta-90 sp-25 an-90 5102 is-17 ta-91 sp-25 an-91 5103 is-17 ta-92 sp-25 an-92 5104 is-17 ta-93 sp-25 an-93 5105 is-17 ta-94 sp-25 an-94 5106 is-17 ta-95 sp-25 an-95 5107 is-17 ta-96 sp-25 an-96 5108 is-17 ta-97 sp-25 an-97 5109 is-17 ta-98 sp-25 an-98 5110 is-17 ta-99 sp-25 an-99 5111 is-17 ta-100 sp-25 an-100 5112 is-17 ta-101 sp-25 an-101 5113 is-17 ta-102 sp-25 an-102 5114 is-17 ta-103 sp-25 an-103 5115 is-17 ta-104 sp-25 an-104 5116 is-17 ta-105 sp-25 an-105 5117 is-17 ta-106 sp-25 an-106 5118 is-17 ta-107 sp-25 an-107 5119 is-17 ta-108 sp-25 an-108 5120 is-17 ta-109 sp-25 an-109 5121 is-17 ta-110 sp-25 an-110 5122 is-17 ta-111 sp-25 an-111 5123 is-17 ta-112 sp-25 an-112 5124 is-17 ta-113 sp-25 an-113 5125 is-17 ta-114 sp-25 an-114 5126 is-17 ta-115 sp-25 an-115 5127 is-17 ta-116 sp-25 an-116 5128 is-17 ta-117 sp-25 an-117 5129 is-17 ta-118 sp-25 an-118 5130 is-17 ta-119 sp-25 an-119 5131 is-17 ta-120 sp-25 an-120 5132 is-17 ta-121 sp-25 an-121 5133 is-17 ta-122 sp-25 an-122 5134 is-17 ta-123 sp-25 an-123 5135 is-17 ta-124 sp-25 an-124 5136 is-17 ta-125 sp-25 an-125 5137 is-17 ta-126 sp-25 an-126 5138 is-17 ta-127 sp-25 an-127 5139 is-17 ta-128 sp-25 an-128 5140 is-17 ta-129 sp-25 an-129 5141 is-17 ta-130 sp-25 an-130 5142 is-17 ta-131 sp-25 an-131 5143 is-17 ta-132 sp-25 an-132 5144 is-17 ta-133 sp-25 an-133 5145 is-17 ta-134 sp-25 an-134 5146 is-17 ta-135 sp-25 an-135 5147 is-17 ta-136 sp-25 an-136 5148 is-17 ta-137 sp-25 an-137 5149 is-17 ta-138 sp-25 an-138 5150 is-17 ta-139 sp-25 an-139 5151 is-17 ta-140 sp-25 an-140 5152 is-17 ta-141 sp-25 an-141 5153 is-17 ta-142 sp-25 an-142 5154 is-17 ta-143 sp-25 an-143 5155 is-17 ta-144 sp-25 an-144 5156 is-17 ta-145 sp-25 an-145 5157 is-17 ta-146 sp-25 an-146 5158 is-17 ta-147 sp-25 an-147 5159 is-17 ta-148 sp-25 an-148 5160 is-17 ta-149 sp-25 an-149 5161 is-17 ta-150 sp-25 an-150 5162 is-17 ta-151 sp-25 an-151 5163 is-17 ta-152 sp-25 an-152 5164 is-17 ta-153 sp-25 an-153 5165 is-17 ta-154 sp-25 an-154 5166 is-17 ta-155 sp-25 an-155 5167 is-17 ta-156 sp-25 an-156 5168 is-17 ta-157 sp-25 an-157 5169 is-17 ta-158 sp-25 an-158 5170 is-17 ta-159 sp-25 an-159 5171 is-17 ta-160 sp-25 an-160 5172 is-17 ta-161 sp-25 an-161 5173 is-17 ta-162 sp-25 an-162 5174 is-17 ta-163 sp-25 an-163 5175 is-17 ta-164 sp-25 an-164 5176 is-17 ta-165 sp-25 an-165 5177 is-17 ta-166 sp-25 an-166 5178 is-17 ta-167 sp-25 an-167 5179 is-17 ta-168 sp-25 an-168 5180 is-17 ta-169 sp-25 an-169 5181 is-17 ta-170 sp-25 an-170 5182 is-17 ta-171 sp-25 an-171 5183 is-17 ta-172 sp-25 an-172 5184 is-17 ta-173 sp-25 an-173 5185 is-17 ta-174 sp-25 an-174 5186 is-17 ta-175 sp-25 an-175 5187 is-17 ta-176 sp-25 an-176 5188 is-17 ta-177 sp-25 an-177 5189 is-17 ta-178 sp-25 an-178 5190 is-17 ta-179 sp-25 an-179 5191 is-17 ta-180 sp-25 an-180 5192 is-17 ta-181 sp-25 an-181 5193 is-17 ta-182 sp-25 an-182 5194 is-17 ta-183 sp-25 an-183 5195 is-17 ta-184 sp-25 an-184 5196 is-17 ta-185 sp-25 an-185 5197 is-17 ta-186 sp-25 an-186 5198 is-17 ta-187 sp-25 an-187 5199 is-17 ta-188 sp-25 an-188 5200 is-17 ta-189 sp-25 an-189 5201 is-17 ta-190 sp-25 an-190 5202 is-17 ta-191 sp-25 an-191 5203 is-17 ta-192 sp-25 an-192 5204 is-17 ta-193 sp-25 an-193 5205 is-17 ta-194 sp-25 an-194 5206 is-17 ta-195 sp-25 an-195 5207 is-17 ta-196 sp-25 an-196 5208 is-17 ta-197 sp-25 an-197 5209 is-17 ta-198 sp-25 an-198 5210 is-17 ta-199 sp-25 an-199 5211 is-17 ta-200 sp-25 an-200 5212 is-17 ta-201 sp-25 an-201 5213 is-17 ta-202 sp-25 an-202 5214 is-17 ta-203 sp-25 an-203 5215 is-17 ta-204 sp-25 an-204 5216 is-17 ta-205 sp-25 an-205 5217 is-17 ta-206 sp-25 an-206 5218 is-17 ta-207 sp-25 an-207 5219 is-17 ta-208 sp-25 an-208 5220 is-17 ta-209 sp-25 an-209 5221 is-17 ta-210 sp-25 an-210 5222 is-17 ta-211 sp-25 an-211 5223 is-17 ta-212 sp-25 an-212 5224 is-17 ta-213 sp-25 an-213 5225 is-17 ta-214 sp-25 an-214 5226 is-17 ta-215 sp-25 an-215 5227 is-17 ta-216 sp-25 an-216 5228 is-17 ta-217 sp-25 an-217 5229 is-17 ta-218 sp-25 an-218 5230 is-17 ta-219 sp-25 an-219 5231 is-17 ta-220 sp-25 an-220 5232 is-17 ta-221 sp-25 an-221 5233 is-17 ta-222 sp-25 an-222 5234 is-17 ta-223 sp-25 an-223 5235 is-17 ta-224 sp-25 an-224 5236 is-17 ta-225 sp-25 an-225 5237 is-17 ta-226 sp-25 an-226 5238 is-17 ta-227 sp-25 an-227 5239 is-17 ta-228 sp-25 an-228 5240 is-17 ta-229 sp-25 an-229 5241 is-17 ta-230 sp-25 an-230 5242 is-17 ta-231 sp-25 an-231 5243 is-17 ta-232 sp-25 an-232 5244 is-17 ta-233 sp-25 an-233 5245 is-17 ta-234 sp-25 an-234 5246 is-17 ta-235 sp-25 an-235 5247 is-17 ta-236 sp-25 an-236 5248 is-17 ta-237 sp-25 an-237 5249 is-17 ta-238 sp-25 an-238 5250 is-17 ta-239 sp-25 an-239 5251 is-17 ta-240 sp-25 an-240 5252 is-17 ta-241 sp-25 an-241 5253 is-17 ta-242 sp-25 an-242 5254 is-17 ta-243 sp-25 an-243 5255 is-17 ta-244 sp-25 an-244 5256 is-17 ta-245 sp-25 an-245 5257 is-17 ta-246 sp-25 an-246 5258 is-17 ta-247 sp-25 an-247 5259 is-17 ta-248 sp-25 an-248 5260 is-17 ta-249 sp-25 an-249 5261 is-17 ta-250 sp-25 an-250 5262 is-17 ta-251 sp-25 an-251 5263 is-17 ta-252 sp-25 an-252 5264 is-17 ta-253 sp-25 an-253 5265 is-17 ta-254 sp-25 an-254 5266 is-17 ta-255 sp-25 an-255 5267 is-17 ta-256 sp-25 an-256 5268 is-17 ta-257 sp-25 an-257 5269 is-17 ta-258 sp-25 an-258 5270 is-17 ta-259 sp-25 an-259 5271 is-17 ta-260 sp-25 an-260 5272 is-17 ta-261 sp-25 an-261 5273 is-17 ta-262 sp-25 an-262 5274 is-17 ta-263 sp-25 an-263 5275 is-17 ta-264 sp-25 an-264 5276 is-17 ta-265 sp-25 an-265 5277 is-17 ta-266 sp-25 an-266 5278 is-17 ta-267 sp-25 an-267 5279 is-17 ta-268 sp-25 an-268 5280 is-17 ta-269 sp-25 an-269 5281 is-17 ta-270 sp-25 an-270 5282 is-17 ta-271 sp-25 an-271 5283 is-17 ta-272 sp-25 an-272 5284 is-17 ta-273 sp-25 an-273 5285 is-17 ta-274 sp-25 an-274 5286 is-17 ta-275 sp-25 an-275 5287 is-17 ta-276 sp-25 an-276 5288 is-17 ta-277 sp-25 an-277 5289 is-17 ta-278 sp-25 an-278 5290 is-17 ta-279 sp-25 an-279 5291 is-17 ta-280 sp-25 an-280 5292 is-17 ta-281 sp-25 an-281 5293 is-17 ta-282 sp-25 an-282 5294 is-17 ta-283 sp-25 an-283 5295 is-17 ta-284 sp-25 an-284 5296 is-17 ta-285 sp-25 an-285 5297 is-17 ta-286 sp-25 an-286 5298 is-17 ta-287 sp-25 an-287 5299 is-17 ta-288 sp-25 an-288 5300 is-17 ta-289 sp-25 an-289 5301 is-17 ta-290 sp-25 an-290 5302 is-17 ta-291 sp-25 an-291 5303 is-17 ta-292 sp-25 an-292 5304 is-17 ta-293 sp-25 an-293 5305 is-17 ta-294 sp-25 an-294 5306 is-17 ta-295 sp-25 an-295 5307 is-17 ta-296 sp-25 an-296 5308 is-17 ta-297 sp-25 an-297 5309 is-17 ta-298 sp-25 an-298 5310 is-17 ta-299 sp-25 an-299 5311 is-17 ta-300 sp-25 an-300 5312 is-17 ta-301 sp-25 an-301 5313 is-17 ta-302 sp-25 an-302 5314 is-17 ta-303 sp-25 an-303 5315 is-17 ta-304 sp-25 an-304 5316 is-17 ta-305 sp-25 an-305 5317 is-17 ta-306 sp-25 an-306 5318 is-17 ta-307 sp-25 an-307 5319 is-17 ta-308 sp-25 an-308 5320 is-17 ta-309 sp-25 an-309 5321 is-17 ta-310 sp-25 an-310 5322 is-17 ta-311 sp-25 an-311 5323 is-17 ta-312 sp-25 an-312 5324 is-17 ta-313 sp-25 an-313 5325 is-17 ta-314 sp-25 an-314 5326 is-17 ta-315 sp-25 an-315 5327 is-17 ta-316 sp-25 an-316 5328 is-17 ta-317 sp-25 an-317 5329 is-17 ta-318 sp-25 an-318 5330 is-17 ta-319 sp-25 an-319 5331 is-17 ta-320 sp-25 an-320 5332 is-17 ta-321 sp-25 an-321 5333 is-17 ta-322 sp-25 an-322 5334 is-17 ta-323 sp-25 an-323 5335 is-17 ta-324 sp-25 an-324 5336 is-17 ta-325 sp-25 an-325 5337 is-17 ta-326 sp-25 an-326 5338 is-17 ta-327 sp-25 an-327 5339 is-17 ta-328 sp-25 an-328 5340 is-17 ta-329 sp-25 an-329 5341 is-17 ta-330 sp-25 an-330 5342 is-17 ta-331 sp-25 an-331 5343 is-17 ta-332 sp-25 an-332 5344 is-17 ta-333 sp-25 an-333 5345 is-17 ta-334 sp-25 an-334 5346 is-17 ta-335 sp-25 an-335 5347 is-17 ta-336 sp-25 an-336 5348 is-17 ta-337 sp-25 an-337 5349 is-17 ta-338 sp-25 an-338 5350 is-17 ta-339 sp-25 an-339 5351 is-17 ta-340 sp-25 an-340 5352 is-17 ta-341 sp-25 an-341 5353 is-17 ta-342 sp-25 an-342 5354 is-17 ta-343 sp-25 an-343 5355 is-17 ta-344 sp-25 an-344 5356 is-17 ta-345 sp-25 an-345 5357 is-17 ta-346 sp-25 an-346 5358 is-17 ta-347 sp-25 an-347 5359 is-17 ta-348 sp-25 an-348 5360 is-17 ta-349 sp-25 an-349 5361 is-17 ta-350 sp-25 an-350 5362 is-17 ta-351 sp-25 an-351 5363 is-17 ta-352 sp-25 an-352 5364 is-17 ta-353 sp-25 an-353 5365 is-17 ta-354 sp-25 an-354 5366 is-17 ta-355 sp-25 an-355 5367 is-17 ta-356 sp-25 an-356 5368 is-17 ta-357 sp-25 an-357 5369 is-17 ta-358 sp-25 an-358 5370 is-17 ta-359 sp-25 an-359 5371 is-17 ta-360 sp-25 an-360 5372 is-17 ta-361 sp-25 an-361 5373 is-17 ta-362 sp-25 an-362 5374 is-17 ta-363 sp-25 an-363 5375 is-17 ta-364 sp-25 an-364 5376 is-17 ta-365 sp-25 an-365 5377 is-17 ta-366 sp-25 an-366 5378 is-17 ta-367 sp-25 an-367 5379 is-17 ta-368 sp-25 an-368 5380 is-17 ta-369 sp-25 an-369 5381 is-17 ta-370 sp-25 an-370 5382 is-17 ta-371 sp-25 an-371 5383 is-17 ta-372 sp-25 an-372 5384 is-17 ta-373 sp-25 an-373 5385 is-17 ta-374 sp-25 an-374 5386 is-17 ta-375 sp-25 an-375 5387 is-17 ta-376 sp-25 an-376 5388 is-17 ta-377 sp-25 an-377 5389 is-17 ta-378 sp-25 an-378 5390 is-17 ta-379 sp-25 an-379 5391 is-17 ta-380 sp-25 an-380 5392 is-17 ta-381 sp-25 an-381 5393 is-17 ta-382 sp-25 an-382 5394 is-17 ta-383 sp-25 an-383 5395 is-17 ta-384 sp-25 an-384 5396 is-17 ta-385 sp-25 an-385 5397 is-17 ta-386 sp-25 an-386 5398 is-17 ta-387 sp-25 an-387 5399 is-17 ta-388 sp-25 an-388 5400 is-17 ta-389 sp-25 an-389 5401 is-17 ta-390 sp-25 an-390 5402 is-17 ta-391 sp-25 an-391 5403 is-17 ta-392 sp-25 an-392 5404 is-17 ta-393 sp-25 an-393 5407 is-14 ta-394 sp-14 an-394 5408 is-14 ta-395 sp-14 an-395 5409 is-14 ta-396 sp-14 an-396 5410 is-14 ta-397 sp-14 an-397 5411 is-14 ta-398 sp-14 an-398 5412 is-14 ta-399 sp-14 an-399 5413 is-14 ta-400 sp-14 an-400 5414 is-14 ta-401 sp-14 an-401 5415 is-14 ta-402 sp-14 an-402 5416 is-14 ta-403 sp-14 an-403 5417 is-14 ta-404 sp-14 an-404 5418 is-14 ta-405 sp-14 an-405 5419 is-14 ta-406 sp-14 an-406 5420 is-14 ta-407 sp-14 an-407 5421 is-15 ta-394 sp-23 an-394 5422 is-15 ta-395 sp-23 an-395 5423 is-15 ta-396 sp-23 an-396 5424 is-15 ta-397 sp-23 an-397 5425 is-15 ta-398 sp-23 an-398 5426 is-15 ta-399 sp-23 an-399 5427 is-15 ta-400 sp-23 an-400 5428 is-15 ta-401 sp-23 an-401 5429 is-15 ta-402 sp-23 an-402 5430 is-15 ta-403 sp-23 an-403 5431 is-15 ta-404 sp-23 an-404 5432 is-15 ta-405 sp-23 an-405 5433 is-15 ta-406 sp-23 an-406 5434 is-15 ta-407 sp-23 an-407 5435 is-17 ta-394 sp-25 an-394 5436 is-17 ta-395 sp-25 an-395 5437 is-17 ta-396 sp-25 an-396 5438 is-17 ta-397 sp-25 an-397 5439 is-17 ta-398 sp-25 an-398 5440 is-17 ta-399 sp-25 an-399 5441 is-17 ta-400 sp-25 an-400 5442 is-17 ta-401 sp-25 an-401 5443 is-17 ta-402 sp-25 an-402 5444 is-17 ta-403 sp-25 an-403 5445 is-17 ta-404 sp-25 an-404 5446 is-17 ta-405 sp-25 an-405 5447 is-17 ta-406 sp-25 an-406 5448 is-17 ta-407 sp-25 an-407

[Examples 3786 to 4064]

As shown in the following formulae,

the procedure in the steps n to p in Example 1 is followed except that the compound obtained in the step m in Example 1, any one of the various acyl halides (ac-1) to (ac-17) represented by the formula (5-1), and any one of the various tertiary amines (ta-1) to (ta-393) represented by the formula (2) are used to obtain compounds of Examples 3786 to 4064 as represented by the formula (1B) as shown in Table 3. In the formula (1B), “-sp-” indicates any one of the (sp-1) to (sp-25) and “-an” indicates any one of the (an-1) to (an-393).

TABLE 3 REACTION COMPOUND OF EX. REAGENT EXAMPLE No. ac ta sp an 3786 ac-3 ta-1 sp-3 an-1 3787 ac-3 ta-2 sp-3 an-2 3788 ac-3 ta-3 sp-3 an-3 3789 ac-3 ta-4 sp-3 an-4 3790 ac-3 ta-5 sp-3 an-5 3791 ac-3 ta-6 sp-3 an-6 3792 ac-3 ta-21 sp-3 an-21 3793 ac-3 ta-25 sp-3 an-25 3794 ac-3 ta-26 sp-3 an-26 3795 ac-3 ta-32 sp-3 an-32 3796 ac-3 ta-34 sp-3 an-34 3797 ac-3 ta-38 sp-3 an-38 3798 ac-3 ta-41 sp-3 an-41 3799 ac-3 ta-42 sp-3 an-42 3800 ac-3 ta-44 sp-3 an-44 3801 ac-3 ta-45 sp-3 an-45 3802 ac-3 ta-47 sp-3 an-47 3803 ac-3 ta-49 sp-3 an-49 3804 ac-3 ta-67 sp-3 an-67 3805 ac-3 ta-88 sp-3 an-88 3806 ac-3 ta-89 sp-3 an-89 3807 ac-3 ta-98 sp-3 an-98 3808 ac-3 ta-99 sp-3 an-99 3809 ac-3 ta-100 sp-3 an-100 3810 ac-3 ta-101 sp-3 an-101 3811 ac-3 ta-107 sp-3 an-107 3812 ac-3 ta-115 sp-3 an-115 3813 ac-3 ta-287 sp-3 an-287 3814 ac-3 ta-288 sp-3 an-288 3815 ac-3 ta-289 sp-3 an-289 3816 ac-3 ta-290 sp-3 an-290 3817 ac-3 ta-291 sp-3 an-291 3818 ac-3 ta-292 sp-3 an-292 3819 ac-3 ta-293 sp-3 an-293 3820 ac-3 ta-294 sp-3 an-294 3821 ac-3 ta-295 sp-3 an-295 3822 ac-3 ta-296 sp-3 an-296 3823 ac-3 ta-297 sp-3 an-297 3824 ac-3 ta-298 sp-3 an-298 3825 ac-3 ta-299 sp-3 an-299 3826 ac-4 ta-1 sp-4 an-1 3827 ac-4 ta-2 sp-4 an-2 3828 ac-4 ta-3 sp-4 an-3 3829 ac-4 ta-4 sp-4 an-4 3830 ac-4 ta-5 sp-4 an-5 3831 ac-4 ta-6 sp-4 an-6 3832 ac-4 ta-21 sp-4 an-21 3833 ac-4 ta-25 sp-4 an-25 3834 ac-4 ta-26 sp-4 an-26 3835 ac-4 ta-32 sp-4 an-32 3836 ac-4 ta-34 sp-4 an-34 3837 ac-4 ta-38 sp-4 an-38 3838 ac-4 ta-41 sp-4 an-41 3839 ac-4 ta-42 sp-4 an-42 3840 ac-4 ta-44 sp-4 an-44 3841 ac-4 ta-45 sp-4 an-45 3842 ac-4 ta-47 sp-4 an-47 3843 ac-4 ta-49 sp-4 an-49 3844 ac-4 ta-67 sp-4 an-67 3845 ac-4 ta-88 sp-4 an-88 3846 ac-4 ta-89 sp-4 an-89 3847 ac-4 ta-98 sp-4 an-98 3848 ac-4 ta-99 sp-4 an-99 3849 ac-4 ta-100 sp-4 an-100 3850 ac-4 ta-101 sp-4 an-101 3851 ac-4 ta-107 sp-4 an-107 3852 ac-4 ta-115 sp-4 an-115 1 ac-4 ta-287 sp-4 an-287 3853 ac-4 ta-288 sp-4 an-288 3854 ac-4 ta-289 sp-4 an-289 3855 ac-4 ta-290 sp-4 an-290 3856 ac-4 ta-291 sp-4 an-291 3857 ac-4 ta-292 sp-4 an-292 3858 ac-4 ta-293 sp-4 an-293 3859 ac-4 ta-294 sp-4 an-294 3860 ac-4 ta-295 sp-4 an-295 3861 ac-4 ta-296 sp-4 an-296 3862 ac-4 ta-297 sp-4 an-297 3863 ac-4 ta-298 sp-4 an-298 3864 ac-4 ta-299 sp-4 an-299 3865 ac-5 ta-1 sp-5 an-1 3866 ac-5 ta-2 sp-5 an-2 3867 ac-5 ta-3 sp-5 an-3 3868 ac-5 ta-4 sp-5 an-4 3869 ac-5 ta-5 sp-5 an-5 3870 ac-5 ta-6 sp-5 an-6 3871 ac-5 ta-21 sp-5 an-21 3872 ac-5 ta-25 sp-5 an-25 3873 ac-5 ta-26 sp-5 an-26 3874 ac-5 ta-32 sp-5 an-32 3875 ac-5 ta-34 sp-5 an-34 3876 ac-5 ta-38 sp-5 an-38 3877 ac-5 ta-41 sp-5 an-41 3878 ac-5 ta-42 sp-5 an-42 3879 ac-5 ta-44 sp-5 an-44 3880 ac-5 ta-45 sp-5 an-45 3881 ac-5 ta-47 sp-5 an-47 3882 ac-5 ta-49 sp-5 an-49 3883 ac-5 ta-67 sp-5 an-67 3884 ac-5 ta-88 sp-5 an-88 3885 ac-5 ta-89 sp-5 an-89 3886 ac-5 ta-98 sp-5 an-98 3887 ac-5 ta-99 sp-5 an-99 3888 ac-5 ta-100 sp-5 an-100 3889 ac-5 ta-101 sp-5 an-101 3890 ac-5 ta-107 sp-5 an-107 3891 ac-5 ta-115 sp-5 an-115 3892 ac-5 ta-287 sp-5 an-287 3893 ac-5 ta-288 sp-5 an-288 3894 ac-5 ta-289 sp-5 an-289 3895 ac-5 ta-290 sp-5 an-290 3896 ac-5 ta-291 sp-5 an-291 3897 ac-5 ta-292 sp-5 an-292 3898 ac-5 ta-293 sp-5 an-293 3899 ac-5 ta-294 sp-5 an-294 3900 ac-5 ta-295 sp-5 an-295 3901 ac-5 ta-296 sp-5 an-296 3902 ac-5 ta-297 sp-5 an-297 3903 ac-5 ta-298 sp-5 an-298 3904 ac-5 ta-299 sp-5 an-299 3905 ac-6 ta-1 sp-6 an-1 3906 ac-6 ta-2 sp-6 an-2 3907 ac-6 ta-3 sp-6 an-3 3908 ac-6 ta-4 sp-6 an-4 3909 ac-6 ta-5 sp-6 an-5 3910 ac-6 ta-6 sp-6 an-6 3911 ac-6 ta-21 sp-6 an-21 3912 ac-6 ta-25 sp-6 an-25 3913 ac-6 ta-26 sp-6 an-26 3914 ac-6 ta-32 sp-6 an-32 3915 ac-6 ta-34 sp-6 an-34 3916 ac-6 ta-38 sp-6 an-38 3917 ac-6 ta-41 sp-6 an-41 3918 ac-6 ta-42 sp-6 an-42 3919 ac-6 ta-44 sp-6 an-44 3920 ac-6 ta-45 sp-6 an-45 3921 ac-6 ta-47 sp-6 an-47 3922 ac-6 ta-49 sp-6 an-49 3923 ac-6 ta-67 sp-6 an-67 3924 ac-6 ta-88 sp-6 an-88 3925 ac-6 ta-89 sp-6 an-89 3926 ac-6 ta-98 sp-6 an-98 3927 ac-6 ta-99 sp-6 an-99 3928 ac-6 ta-100 sp-6 an-100 3929 ac-6 ta-101 sp-6 an-101 3930 ac-6 ta-107 sp-6 an-107 3931 ac-6 ta-115 sp-6 an-115 3932 ac-6 ta-287 sp-6 an-287 3933 ac-6 ta-288 sp-6 an-288 3934 ac-6 ta-289 sp-6 an-289 3935 ac-6 ta-290 sp-6 an-290 3936 ac-6 ta-291 sp-6 an-291 3937 ac-6 ta-292 sp-6 an-292 3938 ac-6 ta-293 sp-6 an-293 3939 ac-6 ta-294 sp-6 an-294 3940 ac-6 ta-295 sp-6 an-295 3941 ac-6 ta-296 sp-6 an-296 3942 ac-6 ta-297 sp-6 an-297 3943 ac-6 ta-298 sp-6 an-298 3944 ac-6 ta-299 sp-6 an-299 3945 ac-7 ta-1 sp-7 an-1 3946 ac-7 ta-2 sp-7 an-2 3947 ac-7 ta-3 sp-7 an-3 3948 ac-7 ta-4 sp-7 an-4 3949 ac-7 ta-5 sp-7 an-5 3950 ac-7 ta-6 sp-7 an-6 3951 ac-7 ta-21 sp-7 an-21 3952 ac-7 ta-25 sp-7 an-25 3953 ac-7 ta-26 sp-7 an-26 3954 ac-7 ta-32 sp-7 an-32 3955 ac-7 ta-34 sp-7 an-34 3956 ac-7 ta-38 sp-7 an-38 3957 ac-7 ta-41 sp-7 an-41 3958 ac-7 ta-42 sp-7 an-42 3959 ac-7 ta-44 sp-7 an-44 3960 ac-7 ta-45 sp-7 an-45 3961 ac-7 ta-47 sp-7 an-47 3962 ac-7 ta-49 sp-7 an-49 3963 ac-7 ta-67 sp-7 an-67 3964 ac-7 ta-88 sp-7 an-88 3965 ac-7 ta-89 sp-7 an-89 3966 ac-7 ta-98 sp-7 an-98 3967 ac-7 ta-99 sp-7 an-99 3968 ac-7 ta-100 sp-7 an-100 3969 ac-7 ta-101 sp-7 an-101 3970 ac-7 ta-107 sp-7 an-107 3971 ac-7 ta-115 sp-7 an-115 3972 ac-7 ta-287 sp-7 an-287 3973 ac-7 ta-288 sp-7 an-288 3974 ac-7 ta-289 sp-7 an-289 3975 ac-7 ta-290 sp-7 an-290 3976 ac-7 ta-291 sp-7 an-291 3977 ac-7 ta-292 sp-7 an-292 3978 ac-7 ta-293 sp-7 an-293 3979 ac-7 ta-294 sp-7 an-294 3980 ac-7 ta-295 sp-7 an-295 3981 ac-7 ta-296 sp-7 an-296 3982 ac-7 ta-297 sp-7 an-297 3983 ac-7 ta-298 sp-7 an-298 3984 ac-7 ta-299 sp-7 an-299 3985 ac-8 ta-1 sp-8 an-1 3986 ac-8 ta-2 sp-8 an-2 3987 ac-8 ta-3 sp-8 an-3 3988 ac-8 ta-4 sp-8 an-4 3989 ac-8 ta-5 sp-8 an-5 3990 ac-8 ta-6 sp-8 an-6 3991 ac-8 ta-21 sp-8 an-21 3992 ac-8 ta-25 sp-8 an-25 3993 ac-8 ta-26 sp-8 an-26 3994 ac-8 ta-32 sp-8 an-32 3995 ac-8 ta-34 sp-8 an-34 3996 ac-8 ta-38 sp-8 an-38 3997 ac-8 ta-41 sp-8 an-41 3998 ac-8 ta-42 sp-8 an-42 3999 ac-8 ta-44 sp-8 an-44 4000 ac-8 ta-45 sp-8 an-45 4001 ac-8 ta-47 sp-8 an-47 4002 ac-8 ta-49 sp-8 an-49 4003 ac-8 ta-67 sp-8 an-67 4004 ac-8 ta-88 sp-8 an-88 4005 ac-8 ta-89 sp-8 an-89 4006 ac-8 ta-98 sp-8 an-98 4007 ac-8 ta-99 sp-8 an-99 4008 ac-8 ta-100 sp-8 an-100 4009 ac-8 ta-101 sp-8 an-101 4010 ac-8 ta-107 sp-8 an-107 4011 ac-8 ta-115 sp-8 an-115 4012 ac-8 ta-287 sp-8 an-287 4013 ac-8 ta-288 sp-8 an-288 4014 ac-8 ta-289 sp-8 an-289 4015 ac-8 ta-290 sp-8 an-290 4016 ac-8 ta-291 sp-8 an-291 4017 ac-8 ta-292 sp-8 an-292 4018 ac-8 ta-293 sp-8 an-293 4019 ac-8 ta-294 sp-8 an-294 4020 ac-8 ta-295 sp-8 an-295 4021 ac-8 ta-296 sp-8 an-296 4022 ac-8 ta-297 sp-8 an-297 4023 ac-8 ta-298 sp-8 an-298 4024 ac-8 ta-299 sp-8 an-299 4025 ac-9 ta-1 sp-9 an-1 4026 ac-9 ta-2 sp-9 an-2 4027 ac-9 ta-3 sp-9 an-3 4028 ac-9 ta-4 sp-9 an-4 4029 ac-9 ta-5 sp-9 an-5 4030 ac-9 ta-6 sp-9 an-6 4031 ac-9 ta-21 sp-9 an-21 4032 ac-9 ta-25 sp-9 an-25 4033 ac-9 ta-26 sp-9 an-26 4034 ac-9 ta-32 sp-9 an-32 4035 ac-9 ta-34 sp-9 an-34 4036 ac-9 ta-38 sp-9 an-38 4037 ac-9 ta-41 sp-9 an-41 4038 ac-9 ta-42 sp-9 an-42 4039 ac-9 ta-44 sp-9 an-44 4040 ac-9 ta-45 sp-9 an-45 4041 ac-9 ta-47 sp-9 an-47 4042 ac-9 ta-49 sp-9 an-49 4043 ac-9 ta-67 sp-9 an-67 4044 ac-9 ta-88 sp-9 an-88 4045 ac-9 ta-89 sp-9 an-89 4046 ac-9 ta-98 sp-9 an-98 4047 ac-9 ta-99 sp-9 an-99 4048 ac-9 ta-100 sp-9 an-100 4049 ac-9 ta-101 sp-9 an-101 4050 ac-9 ta-107 sp-9 an-107 4051 ac-9 ta-115 sp-9 an-115 4052 ac-9 ta-287 sp-9 an-287 4053 ac-9 ta-288 sp-9 an-288 4054 ac-9 ta-289 sp-9 an-289 4055 ac-9 ta-290 sp-9 an-290 4056 ac-9 ta-291 sp-9 an-291 4057 ac-9 ta-292 sp-9 an-292 4058 ac-9 ta-293 sp-9 an-293 4059 ac-9 ta-294 sp-9 an-294 4060 ac-9 ta-295 sp-9 an-295 4061 ac-9 ta-296 sp-9 an-296 4062 ac-9 ta-297 sp-9 an-297 4063 ac-9 ta-298 sp-9 an-298 4064 ac-9 ta-299 sp-9 an-299 End of Table 3

[Example 4065] 1-{5-[4-(3,3-Dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]- pentyl}-1-azoniabicyclo[2.2.2]octafle bromide Step a: Synthesis of 4-methoxybenzoic acid-4-fluorophenyl ester

To a solution of 6.0 g of 4-fluorophenol (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) in 60 ml of chloroform were added 6 ml of triethylamine and a solution of 4.0 g of 4-methoxybenzoyl chloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) in 40 ml of chloroform, and the mixture was stirred at 55° C for 1 hour. The reaction solution was separated by adding to it 100 ml of dichloromethane, 200 ml of water, and 25 ml of a 1N aqueous solution of sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain 8.1 g of the title compound.

Step b: Synthesis of 4-fluoro-2-(4-methoxybenzoyl)phenol

10 ml of titanium tetrachloride (manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.) was added to 6.55 g of the compound obtained in the step a and the mixture was heated at 160° C for 4 hours. Under ice cooling, 10 ml of water was dropwise added to the reaction mixture and further 400 ml of ether and 400 ml of water were added to the mixture at room temperature to separate it. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (8:1) to obtain 3.44 g of the title compound.

Step c: Synthesis of O-[4-fluoro-2-(4-methoxybenzoyl)phenyl]N,N-dimethylthiocarbamate

To a solution of 3.44 g of the compound obtained in the step b in 70 ml of dioxane were added 4.24 g of triethylamine, 0.34 g of dimethylaminopyridine (manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.), and 2.10 g of N,N-dimethylthiocarbamoyl chloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), and the mixture was stirred at 100° C for 24 hours. The reaction suspension was separated by adding to it 200 ml of ethyl acetate and 200 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (3:1) to obtain 4.65 g of the title compound.

Step d: Synthesis of S-[4-fluoro-2-(4-methoxybenzoyl)phenyl]N,N-dimethylthiocarbamate

A suspension of 4.65 g of the compound obtained in the step c in 30 ml of tetradecane (manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.) was heated at 250° C for 5 hours. 12 ml of chloroform was added to the reaction suspension at room temperature to dissolve the reaction product. This solution was charged in a silica gel column and eluted with hexane-ethyl acetate (2:1) to obtain 2.10 g of the title compound.

Step e: Synthesis of 4-fluoro-2-(4-methoxybenzoyl)thiophenol

To a solution of 2.10 g of the compound obtained in the step d in 20 ml of THF were added 20 ml of methanol and 1.88 g of potassium hydroxide, and the mixture was stirred at 60° C for 2 hours. Under ice cooling, 30 ml of 1N hydrochloric acid was dropwise added to the reaction suspension and then 100 ml of ethyl acetate and 100 ml of water were added to the resultant at room temperature to separate it. The organic layer was washed with 150 ml of saturated saline, dried over anhydrous sodium sulfate, and then concentrated to obtain 1.63 g of the title compound.

Step f: Synthesis of 3,3-dibutyl-2,3-dihydro-7-fluoro-5-(4- methoxyphenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps g to i in Example 1 was followed except that the compound obtained in the step e in this example was used to obtain the title compound.

Step g: Synthesis of 3,3-dibutyl-2,3-dihydro-7-dimethylamino-5- (4-methoxyphenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the step k in Example 1 was followed except that the compound obtained in the step fin this example was used to obtain the title compound.

Step h: Synthesis of 3,3-dibutyl-7-dimethylamino-2,3,4,5-tetrahydro-5- (4-methoxyphenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the step m in Example 1 was followed except that the compound obtained in the step g in this example was used to obtain the title compound.

Step i: Synthesis of 3,3-dibutyl-7-dimethylamino-2,3,4,5-tetrahydro-5- (4-hydroxyphenyl)-1,4-benzothiazepine-1,1-dioxide

To a solution of 1.15 g of the compound obtained in the step h in 10 ml of dichloromethane was dropwise added 9 ml of a dichioromethane solution of 1 mol/l boron tribromide (manufactured by ALDRICH CHEMICAL COMPANY) at −20° C and the mixture was stirred under ice cooling for 1 hour. The reaction solution was dropwise added to 200 ml of 5% sodium bicarbonate water under ice cooling. The mixture was then separated by adding to it 100 ml of dichloromethane at room temperature. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (2:1) to obtain 1.00 g of the title compound.

Step j: Trifluoromethanesulfonic acid 4-(3,3-dibutyl-7-dimethylamino- 1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl ester

To a solution of 735 mg of the compound obtained in the step in 3.3 ml of pyridine was dropwise added 388 μl of trifluoromethanesulfonic acid anhydride (manufactured by ALDRICH CHEMICAL COMPANY) at 0° C, and the mixture was stirred at room temperature for 1 hour. The reaction solution was separated by adding to it 10 ml of ethyl acetate and 10 ml of water. The organic layer was washed with 10 ml of saturated aqueous copper sulfate solution, then washed with 10 ml of saturated sodium bicarbonate water, and further washed with 10 ml of saturated saline. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain 916 mg of the title compound.

Step k: Synthesis of 3,3-dibutyl-7-dimethylamino-2,3,4,5-tetrahydro-5- (4-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

To a solution of 3.77 g of the compound obtained in the step j in 38 ml of THF were added 303 mg of palladium II acetate (manufactured by ALDRICH CHEMICAL COMPANY), 986 mg of 2,2-bis- (diphenylphosphenyl)-1,1′-binaphthyl (manufactured by ALDRICH CHEMICAL COMPANY), and 4.42 g of cesium carbonate (manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.). Further, 2.2 ml of benzophenonimine (manufactured by ALDRICH CHEMICAL COMPANY) was added and the mixture was refluxed under heating for 2 hours while stirring. The insoluble matter in the reaction suspension was removed by filtration and the filtrate was concentrated. The residue was dissolved in 65 ml of methanol, and 2.15 g of sodium acetate (manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.) and 1.38 g of hydroxylamine hydrochloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) were added to the solution, and the mixture was stirred at room temperature for 1 hour. The reaction suspension was separated by adding to it 70 ml of dichloromethane and 70 ml of saturated sodium bicarbonate water. The organic layer was washed with 70 ml of saturated saline, dried over anhydrous sodium sulfate, and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (2:1) to obtain 2.48 g of the title compound.

Step l: Synthesis of 1-{5-[4-(3,3-dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]- pentyl}-1-azoniabicyclo[2.2.2]octane bromide

The procedure in the steps n to p was followed except that the compound obtained in the step k in this example was used to obtain the title compound. ¹H-NMR (CDCl₃) δ: 0.85 (3H, t); 0.90 (3H, t); 1.12-1.48 (8H, m); 1.53-2.25 (17H, m); 2.82 (6H, 5); 2.99 (1H, d); 3.10-3.51 (5H, m); 3.61 (6H, t); 5.94 (1H, d); 6.01 (1H, s); 6.47 (1H, dd); 7.41 (2H, d); 7.87 (1H, d); 8.22 (2H, d); 11.62 (1H, s). MS (m/z): 667 (M⁺).

[Example 4066] 1-(3-{3-[4-(3,3-dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1- azoniabicyclo[2.2.2]octane bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step k in Example 4065 was used to obtain the title compound. MS (m/z): 654 (M⁺).

[Example 5405] Benzyl-(4-{3-[4-(3,3-dibutyl-7-dimethylamino-1,1- dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl] thioureido}- benzyl)dimethylammonium bromide Step a: Synthesis of benzyl-(4-isothiocyanatobenzyl)dimethyl- aminonium bromide

The procedure in the step a in Example 9 was followed except that instead of 3-bromopropyl isothiocyanate, 4-(bromomethyl)phenyl isothiocyanate (is-14 mentioned earlier) was used and instead of quinuclidine, N,N-diinethylbenzylainine (ta-32 mentioned earlier) was used to obtain the title compound.

Step b: Synthesis of benzyl-(4-{3-[4-(3,3-dibutyl-7-dimethylamino-1,1- dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}- benzyl)dimethylammonium bromide

The procedure in the step b in Example 9 was followed except that the compound obtained in the step a in this example and the compound obtained in the step k in Example 4065 were used to obtain the title compound.

[Example 5406] 1-(3-{3-[4-(3,3-Dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}benzyl)1- azoniabicyclo[2.2.2]octane bromide Step a: Synthesis of 1-(3-isothiocyanatobenzyl)-1-azoniabicyclo[2.2.2]- octane bromide

The procedure in the step a in Example 9 was followed except that instead of 3-bromopropyl isothiocyanate, 3-(bromomethyl)phenyl isothiocyanate (is-15 mentioned earlier) was used to obtain the title compound.

Step b: Synthesis of 1-(3-{3-[4-(3,3-dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}benzyl)-1- azoniabicyclol2.2.2]octane bromide

The procedure in the step b in Example 9 was followed except that the compound obtained in the step a in this example and the compound obtained in the step k in Example 4065 were used to obtain the title compound.

[Examples 5449 to 5858]

As shown in the following figure,

the procedure in the steps a and b in Example 9 is followed except that any one of the various isothiocyanates (is-14) and (is-17) represented by the formula (5-2b), any one of the various tertiary amines (ta-1) to (ta-407) represented by the formula (2), and the compound obtained in the step b in Example 4 are used to obtain compounds of Examples 5449 to 5858 as represented by the formula (1C) as shown in Table 4. In the formula (1C), “-sp-” indicates any one of the (sp-14) and (sp-25) described above and “-an” indicates any one of the (an-1) to (an-407) described above.

TABLE 4 Example Reagent Example Compound No. is ta sp an 5449 is-14 ta-1  sp-14 an-1  5450 is-14 ta-2  sp-14 an-2  5451 is-14 ta-3  sp-14 an-3  5452 is-14 ta-4  sp-14 an-4  5453 is-14 ta-5  sp-14 an-5  5454 is-14 ta-6  sp-14 an-6  5455 is-14 ta-7  sp-14 an-7  5456 is-14 ta-8  sp-14 an-8  5457 is-14 ta-9  sp-14 an-9  5458 is-14 ta-10  sp-14 an-10  5459 is-14 ta-11  sp-14 an-11  5460 is-14 ta-12  sp-14 an-12  5461 is-14 ta-13  sp-14 an-13  5462 is-14 ta-14  sp-14 an-14  5463 is-14 ta-15  sp-14 an-15  5464 is-14 ta-16  sp-14 an-16  5465 is-14 ta-17  sp-14 an-17  5466 is-14 ta-18  sp-14 an-18  5467 is-14 ta-19  sp-14 an-19  5468 is-14 ta-20  sp-14 an-20  5469 is-14 ta-21  sp-14 an-21  5470 is-14 ta-22  sp-14 an-22  5471 is-14 ta-23  sp-14 an-23  5472 is-14 ta-24  sp-14 an-24  5473 is-14 ta-25  sp-14 an-25  5474 is-14 ta-26  sp-14 an-26  5475 is-14 ta-27  sp-14 an-27  5476 is-14 ta-28  sp-14 an-28  5477 is-14 ta-29  sp-14 an-29  5478 is-14 ta-30  sp-14 an-30  5479 is-14 ta-31  sp-14 an-31  5480 is-14 ta-32  sp-14 an-32  5481 is-14 ta-33  sp-14 an-33  5482 is-14 ta-34  sp-14 an-34  5483 is-14 ta-35  sp-14 an-35  5484 is-14 ta-36  sp-14 an-36  5485 is-14 ta-37  sp-14 an-37  5486 is-14 ta-38  sp-14 an-38  5487 is-14 ta-39  sp-14 an-39  5488 is-14 ta-40  sp-14 an-40  5489 is-14 ta-41  sp-14 an-41  5490 is-14 ta-42  sp-14 an-42  5491 is-14 ta-43  sp-14 an-43  5492 is-14 ta-44  sp-14 an-44  5493 is-14 ta-45  sp-14 an-45  5494 is-14 ta-46  sp-14 an-46  5495 is-14 ta-47  sp-14 an-47  5496 is-14 ta-48  sp-14 an-48  5497 is-14 ta-49  sp-14 an-49  5498 is-14 ta-50  sp-14 an-50  5499 is-14 ta-51  sp-14 an-51  5500 is-14 ta-52  sp-14 an-52  5501 is-14 ta-53  sp-14 an-53  5654 is-14 ta-206 sp-14 an-206 5655 is-14 ta-207 sp-14 an-207 5656 is-14 ta-208 sp-14 an-208 5657 is-14 ta-209 sp-14 an-209 5658 is-14 ta-210 sp-14 an-210 5659 is-14 ta-211 sp-14 an-211 5660 is-14 ta-212 sp-14 an-212 5661 is-14 ta-213 sp-14 an-213 5662 is-14 ta-214 sp-14 an-214 5663 is-14 ta-215 sp-14 an-215 5664 is-14 ta-216 sp-14 an-216 5665 is-14 ta-217 sp-14 an-217 5666 is-14 ta-218 sp-14 an-218 5667 is-14 ta-219 sp-14 an-219 5668 is-14 ta-220 sp-14 an-220 5669 is-14 ta-221 sp-14 an-221 5670 is-14 ta-222 sp-14 an-222 5671 is-14 ta-223 sp-14 an-223 5672 is-14 ta-224 sp-14 an-224 5673 is-14 ta-225 sp-14 an-225 5674 is-14 ta-226 sp-14 an-226 5675 is-14 ta-227 sp-14 an-227 5676 is-14 ta-228 sp-14 an-228 5677 is-14 ta-229 sp-14 an-229 5678 is-14 ta-230 sp-14 an-230 5679 is-14 ta-231 sp-14 an-231 5680 is-14 ta-232 sp-14 an-232 5681 is-14 ta-233 sp-14 an-233 5682 is-14 ta-234 sp-14 an-234 5683 is-14 ta-235 sp-14 an-235 5684 is-14 ta-236 sp-14 an-236 5685 is-14 ta-237 sp-14 an-237 5686 is-14 ta-238 sp-14 an-238 5687 is-14 ta-239 sp-14 an-239 5688 is-14 ta-240 sp-14 an-240 5689 is-14 ta-241 sp-14 an-241 5690 is-14 ta-242 sp-14 an-242 5691 is-14 ta-243 sp-14 an-243 5692 is-14 ta-244 sp-14 an-244 5693 is-14 ta-245 sp-14 an-245 5694 is-14 ta-246 sp-14 an-246 5695 is-14 ta-247 sp-14 an-247 5696 is-14 ta-248 sp-14 an-248 5697 is-14 ta-249 sp-14 an-249 5698 is-14 ta-250 sp-14 an-250 5699 is-14 ta-251 sp-14 an-251 5700 is-14 ta-252 sp-14 an-252 5701 is-14 ta-253 sp-14 an-253 5702 is-14 ta-254 sp-14 an-254 5703 is-14 ta-255 sp-14 an-255 5704 is-14 ta-256 sp-14 an-256 5705 is-14 ta-257 sp-14 an-257 5706 is-14 ta-258 sp-14 an-258 5449 is-14 ta-1  sp-14 an-1  5450 is-14 ta-2  sp-14 an-2  5451 is-14 ta-3  sp-14 an-3  5452 is-14 ta-4  sp-14 an-4  5453 is-14 ta-5  sp-14 an-5  5454 is-14 ta-6  sp-14 an-6  5455 is-14 ta-7  sp-14 an-7  5456 is-14 ta-8  sp-14 an-8  5457 is-14 ta-9  sp-14 an-9  5458 is-14 ta-10  sp-14 an-10  5459 is-14 ta-11  sp-14 an-11  5460 is-14 ta-12  sp-14 an-12  5461 is-14 ta-13  sp-14 an-13  5462 is-14 ta-14  sp-14 an-14  5463 is-14 ta-15  sp-14 an-15  5464 is-14 ta-16  sp-14 an-16  5465 is-14 ta-17  sp-14 an-17  5466 is-14 ta-18  sp-14 an-18  5467 is-14 ta-19  sp-14 an-19  5468 is-14 ta-20  sp-14 an-20  5469 is-14 ta-21  sp-14 an-21  5470 is-14 ta-22  sp-14 an-22  5471 is-14 ta-23  sp-14 an-23  5472 is-14 ta-24  sp-14 an-24  5473 is-14 ta-25  sp-14 an-25  5474 is-14 ta-26  sp-14 an-26  5475 is-14 ta-27  sp-14 an-27  5476 is-14 ta-28  sp-14 an-28  5477 is-14 ta-29  sp-14 an-29  5478 is-14 ta-30  sp-14 an-30  5479 is-14 ta-31  sp-14 an-31  5480 is-14 ta-32  sp-14 an-32  5481 is-14 ta-33  sp-14 an-33  5482 is-14 ta-34  sp-14 an-34  5483 is-14 ta-35  sp-14 an-35  5484 is-14 ta-36  sp-14 an-36  5485 is-14 ta-37  sp-14 an-37  5486 is-14 ta-38  sp-14 an-38  5487 is-14 ta-39  sp-14 an-39  5488 is-14 ta-40  sp-14 an-40  5489 is-14 ta-41  sp-14 an-41  5490 is-14 ta-42  sp-14 an-42  5491 is-14 ta-43  sp-14 an-43  5492 is-14 ta-44  sp-14 an-44  5493 is-14 ta-45  sp-14 an-45  5494 is-14 ta-46  sp-14 an-46  5495 is-14 ta-47  sp-14 an-47  5496 is-14 ta-48  sp-14 an-48  5497 is-14 ta-49  sp-14 an-49  5498 is-14 ta-50  sp-14 an-50  5499 is-14 ta-51  sp-14 an-51  5500 is-14 ta-52  sp-14 an-52  5501 is-14 ta-53  sp-14 an-53  5654 is-14 ta-206 sp-14 an-206 5655 is-14 ta-207 sp-14 an-207 5656 is-14 ta-208 sp-14 an-208 5657 is-14 ta-209 sp-14 an-209 5658 is-14 ta-210 sp-14 an-210 5659 is-14 ta-211 sp-14 an-211 5660 is-14 ta-212 sp-14 an-212 5661 is-14 ta-213 sp-14 an-213 5662 is-14 ta-214 sp-14 an-214 5663 is-14 ta-215 sp-14 an-215 5664 is-14 ta-216 sp-14 an-216 5665 is-14 ta-217 sp-14 an-217 5666 is-14 ta-218 sp-14 an-218 5667 is-14 ta-219 sp-14 an-219 5668 is-14 ta-220 sp-14 an-220 5669 is-14 ta-221 sp-14 an-221 5670 is-14 ta-222 sp-14 an-222 5671 is-14 ta-223 sp-14 an-223 5672 is-14 ta-224 sp-14 an-224 5673 is-14 ta-225 sp-14 an-225 5674 is-14 ta-226 sp-14 an-226 5675 is-14 ta-227 sp-14 an-227 5676 is-14 ta-228 sp-14 an-228 5677 is-14 ta-229 sp-14 an-229 5678 is-14 ta-230 sp-14 an-230 5679 is-14 ta-231 sp-14 an-231 5680 is-14 ta-232 sp-14 an-232 5681 is-14 ta-233 sp-14 an-233 5682 is-14 ta-234 sp-14 an-234 5683 is-14 ta-235 sp-14 an-235 5684 is-14 ta-236 sp-14 an-236 5685 is-14 ta-237 sp-14 an-237 5686 is-14 ta-238 sp-14 an-238 5687 is-14 ta-239 sp-14 an-239 5688 is-14 ta-240 sp-14 an-240 5689 is-14 ta-241 sp-14 an-241 5690 is-14 ta-242 sp-14 an-242 5691 is-14 ta-243 sp-14 an-243 5692 is-14 ta-244 sp-14 an-244 5693 is-14 ta-245 sp-14 an-245 5694 is-14 ta-246 sp-14 an-246 5695 is-14 ta-247 sp-14 an-247 5696 is-14 ta-248 sp-14 an-248 5697 is-14 ta-249 sp-14 an-249 5698 is-14 ta-250 sp-14 an-250 5699 is-14 ta-251 sp-14 an-251 5700 is-14 ta-252 sp-14 an-252 5701 is-14 ta-253 sp-14 an-253 5702 is-14 ta-254 sp-14 an-254 5703 is-14 ta-255 sp-14 an-255 5704 is-14 ta-256 sp-14 an-256 5705 is-14 ta-257 sp-14 an-257 5706 is-14 ta-258 sp-14 an-258 5449 is-14 ta-1  sp-14 an-1  5450 is-14 ta-2  sp-14 an-2  5451 is-14 ta-3  sp-14 an-3  5452 is-14 ta-4  sp-14 an-4  5453 is-14 ta-5  sp-14 an-5  5454 is-14 ta-6  sp-14 an-6  5455 is-14 ta-7  sp-14 an-7  5456 is-14 ta-8  sp-14 an-8  5457 is-14 ta-9  sp-14 an-9  5458 is-14 ta-10  sp-14 an-10  5459 is-14 ta-11  sp-14 an-11  5460 is-14 ta-12  sp-14 an-12  5461 is-14 ta-13  sp-14 an-13  5462 is-14 ta-14  sp-14 an-14  5463 is-14 ta-15  sp-14 an-15  5464 is-14 ta-16  sp-14 an-16  5465 is-14 ta-17  sp-14 an-17  5466 is-14 ta-18  sp-14 an-18  5467 is-14 ta-19  sp-14 an-19  5468 is-14 ta-20  sp-14 an-20  5469 is-14 ta-21  sp-14 an-21  5470 is-14 ta-22  sp-14 an-22  5471 is-14 ta-23  sp-14 an-23  5472 is-14 ta-24  sp-14 an-24  5473 is-14 ta-25  sp-14 an-25  5474 is-14 ta-26  sp-14 an-26  5475 is-14 ta-27  sp-14 an-27  5476 is-14 ta-28  sp-14 an-28  5477 is-14 ta-29  sp-14 an-29  5478 is-14 ta-30  sp-14 an-30  5479 is-14 ta-31  sp-14 an-31  5480 is-14 ta-32  sp-14 an-32  5481 is-14 ta-33  sp-14 an-33  5482 is-14 ta-34  sp-14 an-34  5483 is-14 ta-35  sp-14 an-35  5484 is-14 ta-36  sp-14 an-36  5485 is-14 ta-37  sp-14 an-37  5486 is-14 ta-38  sp-14 an-38  5487 is-14 ta-39  sp-14 an-39  5488 is-14 ta-40  sp-14 an-40  5489 is-14 ta-41  sp-14 an-41  5490 is-14 ta-42  sp-14 an-42  5491 is-14 ta-43  sp-14 an-43  5492 is-14 ta-44  sp-14 an-44  5493 is-14 ta-45  sp-14 an-45  5494 is-14 ta-46  sp-14 an-46  5495 is-14 ta-47  sp-14 an-47  5496 is-14 ta-48  sp-14 an-48  5497 is-14 ta-49  sp-14 an-49  5498 is-14 ta-50  sp-14 an-50  5499 is-14 ta-51  sp-14 an-51  5500 is-14 ta-52  sp-14 an-52  5501 is-14 ta-53  sp-14 an-53  5654 is-14 ta-206 sp-14 an-206 5655 is-14 ta-207 sp-14 an-207 5656 is-14 ta-208 sp-14 an-208 5657 is-14 ta-209 sp-14 an-209 5658 is-14 ta-210 sp-14 an-210 5659 is-14 ta-211 sp-14 an-211 5660 is-14 ta-212 sp-14 an-212 5661 is-14 ta-213 sp-14 an-213 5662 is-14 ta-214 sp-14 an-214 5663 is-14 ta-215 sp-14 an-215 5664 is-14 ta-216 sp-14 an-216 5665 is-14 ta-217 sp-14 an-217 5666 is-14 ta-218 sp-14 an-218 5667 is-14 ta-219 sp-14 an-219 5668 is-14 ta-220 sp-14 an-220 5669 is-14 ta-221 sp-14 an-221 5670 is-14 ta-222 sp-14 an-222 5671 is-14 ta-223 sp-14 an-223 5672 is-14 ta-224 sp-14 an-224 5673 is-14 ta-225 sp-14 an-225 5674 is-14 ta-226 sp-14 an-226 5675 is-14 ta-227 sp-14 an-227 5676 is-14 ta-228 sp-14 an-228 5677 is-14 ta-229 sp-14 an-229 5678 is-14 ta-230 sp-14 an-230 5679 is-14 ta-231 sp-14 an-231 5680 is-14 ta-232 sp-14 an-232 5681 is-14 ta-233 sp-14 an-233 5682 is-14 ta-234 sp-14 an-234 5683 is-14 ta-235 sp-14 an-235 5684 is-14 ta-236 sp-14 an-236 5685 is-14 ta-237 sp-14 an-237 5686 is-14 ta-238 sp-14 an-238 5687 is-14 ta-239 sp-14 an-239 5688 is-14 ta-240 sp-14 an-240 5689 is-14 ta-241 sp-14 an-241 5690 is-14 ta-242 sp-14 an-242 5691 is-14 ta-243 sp-14 an-243 5692 is-14 ta-244 sp-14 an-244 5693 is-14 ta-245 sp-14 an-245 5694 is-14 ta-246 sp-14 an-246 5695 is-14 ta-247 sp-14 an-247 5696 is-14 ta-248 sp-14 an-248 5697 is-14 ta-249 sp-14 an-249 5698 is-14 ta-250 sp-14 an-250 5699 is-14 ta-251 sp-14 an-251 5700 is-14 ta-252 sp-14 an-252 5701 is-14 ta-253 sp-14 an-253 5702 is-14 ta-254 sp-14 an-254 5703 is-14 ta-255 sp-14 an-255 5704 is-14 ta-256 sp-14 an-256 5705 is-14 ta-257 sp-14 an-257 5706 is-14 ta-258 sp-14 an-258 5449 is-14 ta-1  sp-14 an-1  5450 is-14 ta-2  sp-14 an-2  5451 is-14 ta-3  sp-14 an-3  5452 is-14 ta-4  sp-14 an-4  5453 is-14 ta-5  sp-14 an-5  5454 is-14 ta-6  sp-14 an-6  5455 is-14 ta-7  sp-14 an-7  5456 is-14 ta-8  sp-14 an-8  5457 is-14 ta-9  sp-14 an-9  5458 is-14 ta-10  sp-14 an-10  5459 is-14 ta-11  sp-14 an-11  5460 is-14 ta-12  sp-14 an-12  5461 is-14 ta-13  sp-14 an-13  5462 is-14 ta-14  sp-14 an-14  5463 is-14 ta-15  sp-14 an-15  5464 is-14 ta-16  sp-14 an-16  5465 is-14 ta-17  sp-14 an-17  5466 is-14 ta-18  sp-14 an-18  5467 is-14 ta-19  sp-14 an-19  5468 is-14 ta-20  sp-14 an-20  5469 is-14 ta-21  sp-14 an-21  5470 is-14 ta-22  sp-14 an-22  5471 is-14 ta-23  sp-14 an-23  5472 is-14 ta-24  sp-14 an-24  5473 is-14 ta-25  sp-14 an-25  5474 is-14 ta-26  sp-14 an-26  5475 is-14 ta-27  sp-14 an-27  5476 is-14 ta-28  sp-14 an-28  5477 is-14 ta-29  sp-14 an-29  5478 is-14 ta-30  sp-14 an-30  5479 is-14 ta-31  sp-14 an-31  5480 is-14 ta-32  sp-14 an-32  5481 is-14 ta-33  sp-14 an-33  5482 is-14 ta-34  sp-14 an-34  5483 is-14 ta-35  sp-14 an-35  5484 is-14 ta-36  sp-14 an-36  5485 is-14 ta-37  sp-14 an-37  5486 is-14 ta-38  sp-14 an-38  5487 is-14 ta-39  sp-14 an-39  5488 is-14 ta-40  sp-14 an-40  5489 is-14 ta-41  sp-14 an-41  5490 is-14 ta-42  sp-14 an-42  5491 is-14 ta-43  sp-14 an-43  5492 is-14 ta-44  sp-14 an-44  5493 is-14 ta-45  sp-14 an-45  5494 is-14 ta-46  sp-14 an-46  5495 is-14 ta-47  sp-14 an-47  5496 is-14 ta-48  sp-14 an-48  5497 is-14 ta-49  sp-14 an-49  5498 is-14 ta-50  sp-14 an-50  5499 is-14 ta-51  sp-14 an-51  5500 is-14 ta-52  sp-14 an-52  5501 is-14 ta-53  sp-14 an-53  5654 is-14 ta-206 sp-14 an-206 5655 is-14 ta-207 sp-14 an-207 5656 is-14 ta-208 sp-14 an-208 5657 is-14 ta-209 sp-14 an-209 5658 is-14 ta-210 sp-14 an-210 5659 is-14 ta-211 sp-14 an-211 5660 is-14 ta-212 sp-14 an-212 5661 is-14 ta-213 sp-14 an-213 5662 is-14 ta-214 sp-14 an-214 5663 is-14 ta-215 sp-14 an-215 5664 is-14 ta-216 sp-14 an-216 5665 is-14 ta-217 sp-14 an-217 5666 is-14 ta-218 sp-14 an-218 5667 is-14 ta-219 sp-14 an-219 5668 is-14 ta-220 sp-14 an-220 5669 is-14 ta-221 sp-14 an-221 5670 is-14 ta-222 sp-14 an-222 5671 is-14 ta-223 sp-14 an-223 5672 is-14 ta-224 sp-14 an-224 5673 is-14 ta-225 sp-14 an-225 5674 is-14 ta-226 sp-14 an-226 5675 is-14 ta-227 sp-14 an-227 5676 is-14 ta-228 sp-14 an-228 5677 is-14 ta-229 sp-14 an-229 5678 is-14 ta-230 sp-14 an-230 5679 is-14 ta-231 sp-14 an-231 5680 is-14 ta-232 sp-14 an-232 5681 is-14 ta-233 sp-14 an-233 5682 is-14 ta-234 sp-14 an-234 5683 is-14 ta-235 sp-14 an-235 5684 is-14 ta-236 sp-14 an-236 5685 is-14 ta-237 sp-14 an-237 5686 is-14 ta-238 sp-14 an-238 5687 is-14 ta-239 sp-14 an-239 5688 is-14 ta-240 sp-14 an-240 5689 is-14 ta-241 sp-14 an-241 5690 is-14 ta-242 sp-14 an-242 5691 is-14 ta-243 sp-14 an-243 5692 is-14 ta-244 sp-14 an-244 5693 is-14 ta-245 sp-14 an-245 5694 is-14 ta-246 sp-14 an-246 5695 is-14 ta-247 sp-14 an-247 5696 is-14 ta-248 sp-14 an-248 5697 is-14 ta-249 sp-14 an-249 5698 is-14 ta-250 sp-14 an-250 5699 is-14 ta-251 sp-14 an-251 5700 is-14 ta-252 sp-14 an-252 5701 is-14 ta-253 sp-14 an-253 5702 is-14 ta-254 sp-14 an-254 5703 is-14 ta-255 sp-14 an-255 5704 is-14 ta-256 sp-14 an-256 5705 is-14 ta-257 sp-14 an-257 5706 is-14 ta-258 sp-14 an-258

[Test Example 1]

Blood cholesterol lowering effect in rats fed on a high cholesterol diet

In this test example, blood cholesterol level lowering effect in rats fed on a high cholesterol diet was tested according to the method described in J. Lipid, Res., 1995, 36, 1098-1105.

That is, a diet containing 0.4% cholesterol and 0.5% of bile acid was given to 7 to 9 weeks old SD (IGS) male rats for 5 days before the test to increase the blood cholesterol level. Rats which showed an evident increase in blood cholesterol level as compared with that before feeding were selected and used in the test. Cholestimide (trade name: CHOLEBINE GRANULE 70% manufactured by MITSUBISHI TOKYO PHARMACEUTICALS, INC.), which is an anion exchange resin, was suspended in distilled water while the test compound was either dissolved or suspended in distilled water. These were forcibly orally administered twice a day every day from the day of beginning of the test (each n =8). After 3 hours from the administration of the drug on the last day of the test, a blood sample was taken from a jugular vein pool and serum cholesterol level was measured to study the effect of the test compound. Further, as a control group, a group (n=8) fed on only high cholesterol diet and given distilled water (1 ml/kg) was prepared and the same test procedure was followed. A commercially available kit was used for the measurement of total cholesterol and HDL cholesterol. The value obtained by subtracting an HDL cholesterol value from the total cholesterol value was taken as an LDL+VLDL cholesterol value. Assuming the LDL+VLDL cholesterol value of the control group, for which the test compound was not used, as 100%, the rate of decrease (percentage of decrease) of LDL+VLDL cholesterol value when a fixed amount of the test compound was used, was determined.

The results are shown in Table 5 below. It has been verified that the compounds of the present invention decrease the LDL+VLDL cholesterol level and have excellent blood cholesterol lowering effect. Therefore, the compounds of the present invention have proved to be useful as drugs for the treatment and prevention of hyperlipidemia. Moreover, it has been verified that the compounds of the present invention have an inhibitory effect on increase of cholesterol even when a diet containing 0.4% cholesterol and 0.5% bile acid is fed and at the same time the compound of the present invention was forcibly orally administered, so that the compounds of the present invention are useful as drug for the prevention of hyperlipidemia. Note that it has also been verified that the compounds of other examples of the present invention not shown in Table 5 have excellent blood cholesterol lowering effect and thus the compounds have proved to be useful in particular as drugs for the treatment and prevention of hyperlipidemia.

TABLE 5 Rat model loaded with high cholesterol diet (treatment model) Rate of decrease (%) of LDL + VLDL Dosage of drug at a time is indicated Compound in example in parenthesis Comparative Example* 29.0 (25 mg/kg) Example 1 68.4 (1 mg/kg) Example 1 49 (0.3 mg/kg) Example 3713 41 (0.3 mg/kg) Example 3747 48 (0.3 mg/kg) Example 3752 50 (0.3 mg/kg) Example 5408 43 (0.3 mg/kg) Example 3696 25 (0.3 mg/kg) Example 3440 36 (0.3 mg/kg) Example 3448 20 (0.3 mg/kg) Example 3605 28 (0.3 mg/kg) *In Comparative Example, Cholestimide (trade name: CHOLEBINE KARYU 70% manufactured by MITSUBISHI TOKYO PHARMACEUTICALS, INC.) was used.

[Test Example 2]

Bile acid-decreasing effect in portal vein of rats loaded with cholic acid

In this test example, the test for confirming the bile acid-decreasing effect in portal vein of cholic acid-loaded rats was carried out according to the method described in Pharmacology and Therapeutics [Jpn Pharmacol. Ther., Vol. 24 Supplement, 1996, 103 (S-577)-110 (S-584)].

That is, 7 to 9 weeks old SD (IGS) rats were starved on the day before the test and thereafter. Cholic acid (200 mg/kg) and the test compound as drug to be administered, were either dissolved or suspended in distilled water containing a surfactant (trade name: Tween 20, BIO-RAD or HCO-60, manufactured by NIPPON CHEMICALS COMPANY, LTD.) to a final concentration of 0.5% or 1% and the solution or suspension was forcibly orally administered to the rats. After 2 hours from the administration, a sample of blood was taken from a portal vein and total serum bile acid level was measured to study the effect of the test compound (n=6). Further, as a control group, a group (n=6) loaded with cholic acid (200 mg/kg) only was prepared and the same test procedure was followed. A commercially available kit (trade name: SOTANJUSAN-TEST WAKO-(SOTANJUSAN=total bile acid), manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.) was used for the measurement of bile acid. Assuming the value of the control group, which is a group in which no test compound was used, as 100%, the rate of decrease (percentage (%) of decrease) of the bile acid level when a fixed amount of the test compound was used was determined.

The results are shown in Table 6 below. It has been verified that the compounds of the present invention decrease the bile acid level and proved to have excellent bile acid resorption inhibiting effect. Therefore, it has been verified that the compounds of the present invention are useful as drugs for the treatment and prevention of hyperlipidemia and further useful as drugs for the treatment of cholestasis-caused hepatopathy. Note that it has also been verified that the compounds of other examples of the present invention not shown in Table 6 below have excellent bile acid resorption inhibiting effects and thus the compounds of the present invention have proved to be useful as drugs for the treatment and prevention of hyperlipidemia and as drugs for the treatment of cholestasis-caused hepatopathy.

TABLE 6 Cholic acid-loaded rat model Rate of decrease (%) of bile acid Dosage of drug at a time is Compound of Example indicated in parenthesis Comparative Example 1* 16 (25 mg/kg) # Comparative Example 2** 3 (0.1 mg/kg) # Example 3835 23 (0.1 mg/kg) # Example 1 51 (0.1 mg/kg) # Example 3932 30 (0.1 mg/kg) # Example 9 13 (0.1 mg/kg) # Example 425 21 (0.1 mg/kg) # Example 801 33 (0.1 mg/kg) ## Example 1178 18 (0.1 mg/kg) ## Example 3440 26 (0.1 mg/kg) ## Example 3695 23 (0.1 mg/kg) ## Example 3853 36 (0.1 mg/kg) ## Example 3607 36 (0.1 mg/kg) ## Example 3608 43 (0.1 mg/kg) ## Example 5405 16 (0.1 mg/kg) ## Example 4512 37 (0.1 mg/kg) ## Example 4257 30 (0.1 mg/kg) ## Example 4424 17 (0.1 mg/kg) ## Example 4425 22 (0.1 mg/kg) ## Example 4905 28 (0.1 mg/kg) ## Example 3696 13 (0.1 mg/kg) ## Example 3605 24 (0.1 mg/kg) ## Example 3475 19 (0.1 mg/kg) ## Example 3448 25 (0.1 mg/kg) ## Example 5406 15 (0.1 mg/kg) ## Example 3409 28 (0.1 mg/kg) ## Example 3783 16 (0.1 mg/kg) ## Example 3710 20 (0.1 mg/kg) ## Example 3713 32 (0.1 mg/kg) ## Example 3753 8.5 (0.3 mg/kg) ## Example 3759 36 (0.3 mg/kg) ## Example 5043 39 (0.3 mg/kg) ## Example 5298 40 (0.3 mg/kg) ## Example 3747 40 (0.1 mg/kg) ## Example 3752 42 (0.1 mg/kg) ## Example 5408 35 (0.1 mg/kg) ## *In Comparative Example 1, Cholestimide (trade name: CHOLEBINE KARYU (GRANULATED POWDER) 70% manufactured by MITSUBISHI TOKYO PHARMACEUTICALS, INC.) was used. **In Comparative Example 2, compound 5 that shows the most potent activity among the compounds specifically described in WO02/08211 (synthesis Example 19); 1-{4-[4-(3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenoxymethyl]benzyl}-4-aza-1-azoniabicyclo[2.2.2]octance chloride (compound A mentioned later was used). # Tween 20 having a final concentration of 0.05% was used as a surfactant. ## HCO-60 having a final concentration of 0.1% was used as a surfactant.

[Test Example 3]

Effect on rat liver cholesterol 7-α-hydroxylase activity (7α-OHase)

In this test example, the test for confirming the effect on rat liver cholesterol 7-α-hydroxylase activity (7α-OHase) was carried out according to the method described in [Analytical Biochemistry, 1986, 158, 228-232].

That is, the test compound and vehicle (injectable water, trade name: manufactured by OHTSUKA PHARMACEUTICAL CO., LTD.) were administered to 6 weeks old SD (IGS) rats using an oral sonde for 14 days (n=5). Solid diet (trade name: CRF-1, manufactured by ORIENTAL YEAST CO., LTD.) was given as a diet and a sterilized tap water was given as drink water, and the rats were allowed to take them freely. The rats were dissected and the livers were extracted. The livers were preserved temporarily at −80° C. Thawed liver samples were homogenized in 1.15% KCl and then centrifuged to prepare liver microsomes. Final pelletized materials were resuspended in a buffer solution of sodium phosphate/potassium phosphate, followed by incubation of an aliquot at 37° C for 20 minutes in the presence of NADPH. The 7α-hydroxy-cholesterol formed was converted into 7α-hydroxy-4-cholesten-3-one by cholesterol oxidase. After extraction of this in petroleum ether, the organic solvent was evaporated and the residue was dissolved in isopropanol. An enzyme product was separated by injecting the aliquot of the extract into a reverse phase HPLC column (trade name: Finepack SIL-5, JASCO) and the substance eluted was quantated by using a 240 nm UV detector.

It has been verified that the compounds of the present invention have potent enhancing effects on the activity of liver cholesterol 7-α-hydroxylase (7α-OHase) which is included in the mechanism of blood cholesterol-lowering effects (Arterioscler Thromb Vasc. Biol., 1998, 18, 1304-1311) due to IBAT, which is an ileal bile acid transporter and that the compounds of the present invention can be used as drugs for the treatment and prevention of hyperlipidemia and so forth.

[Test example 4]

Cholestasis-caused hepatopathy (liver cell apoptosis) model

The “cholestasis-caused hepatopathy” model in this test example was handled by referring to apoptosis induction in liver cells of hypercholesterolemia model described in [Am. J. Physiol., 1995, 268, G613-G621].

That is, a diet containing 0.4% of cholesterol and 0.5% of bile acid was given to 7 to 9 weeks old SD (IGS) male rats for 4 days. The test compounds were forcibly orally administered twice a day everyday from the day of starting of feeding with the high cholesterol diet (n=8). As a control group, a group (n=8) fed with only the high cholesterol diet was prepared. After 3 hours from the administration of the drug on the last day of the experiment, the livers were extracted from the rats immediately after bloodletting from the abdominal aorta and fixed with a 10% neutral buffered formalin solution (trade name: FA-F96 manufactured by KOKUSAN CHEMICAL CO, LTD.). After the fixation, the livers were dewatered and embedded by use of a closed automatic embedding apparatus (trade name: ETP-180B, manufactured by SAKURA CO., LTD.) and thin slices of a thickness within the range of 2 μm to 5 μm were prepared with a microtome (trade name; IVS-410, manufactured by SAKURA CO., LTD.). Then, hematoxylin-eosin staining was performed on these thin sections using an automatic dyeing apparatus (trade name: DRS-60, manufactured by SAKURA CO. LTD.). Total number of mitotic cells in each slice was obtained by measuring for each section the number of mitotic cells at 10 different places in an area of 200 μm×200 μm in the same section.

The results are shown in Table 7 below. It has been verified that the compounds of the present invention exhibit a decreased number of mitotic cells in the liver and have effects of ameliorating cholestasis-caused hepatopathy. Therefore, the compounds of the present invention have proven to be useful as drugs for the treatment and prevention of cholestasis-caused hepatopathy.

TABLE 7 Number of mitotic cells in liver (average ± standard error, n = 8) In parenthesis, dosage of drug at a Compound of Example time is indicated. Example 1 50 ± 13 (control group) 28 ± 7  (1 mg/kg) 36 ± 13 (0.1 mg/kg)

[Test Example 5]

“Cholestasis-caused hepatopathy” model (bile duct partial ligation model)

The “cholestasis-caused hepatopathy” model by partial ligation surgery of bile duct in this test example was handled by referring to the method by Kanno et al. [Kanzo (Liver) 43 Suppl (1): A126, 2002].

That is, the abdomen of a 7 to 10 weeks old SD (IGS) male rat was cut open under anesthesia with pentobarbital and partial ligation surgery of the bile duct was carried out. A blood sample was taken from the femoral vein before the surgery and this was taken as pre-administration value. The test compound and 200 mg/kg of bile acid were forcibly orally administered twice a day for 3.5 days from the next day of the surgery (protocol A). The test compound and 200 mg/kg of bile acid were forcibly orally administered twice a day for 3.5 days without carrying out the partial ligation surgery (protocol B). In both the cases, the test compound was dissolved or suspended in distilled water or an aqueous solution of 1% HCO60 (manufactured by NIPPON CHEMICALS COMPANY, LTD.). Physiological saline was administered to a control group, while 25 mg/kg of cholestyramine (manufactured by SIGMA CHEMICAL COMPANY) or 50 mg/kg of ursodeoxycholic acid (manufactured by MITSUBISHI PHARMA CO., LTD.) as a comparative example was administered. Moreover, to consider the influence of the surgery, a pseudo operation group (a Sham group) was established as necessary. After 6 hours from the administration of the drug on the last day of the test, a blood sample was taken from the abdominal aorta and AST (GOT), ALT (GPT), and ALP in the blood were measured by using a measurement kit (GOTII-HA TEST WAKO, GPTII-HA TEST WAKO, and ALKALINE PHOSPHER-HA TEST WAKO respectively, all manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.) with an auto analyzer (NITTECH ANALYZER SUPER Z818).

The results are shown in Tables 8 to 10 below. It has been verified that the compounds of the present invention inhibit the rise in AST, ALT, and ALP caused by partial ligation of the liver and loading of bile acid and have effects of ameliorating cholestasis-caused hepatopathy. Therefore, the compounds of the present invention have proved to be useful as drugs for the treatment and prevention of cholestasis-caused hepatopathy, in particular as drugs for the treatment and prevention of primary biliary cirrhosis and primary sclerosing cholangitis. Moreover, it has also been verified that the compounds of other examples of the present invention not shown in Tables 8 to 10 have excellent ameliorating effect on cholestasis-caused hepatopathy.

TABLE 8 (Protocol A) Compound of AST ALT ALP Example (IU/L) (IU/L) (IU/L) (Pre-administration 108 ± 6 38 ± 2  591 ± 116 value) Control group 400 ± 160 200 ± 81  1120 ± 410  Comparative 385 ± 214 208 ± 123 1280 ± 660  Example 1 Comparative 256 ± 64 98 ± 25 785 ± 120 Example 2 Example 1 182 ± 42 61 ± 4  603 ± 78  (0.1 mg/kg) (For all the cases, N = 8, average ± standard error) In Comparative Example 1, 25 mg/kg of cholestyramine was administered while in Comparative Example 2, 50 mg/kg of ursodeoxycholic acid was administered. Distilled water was used as a solvent.

TABLE 9 (Protocol A) Compound of Example AST (IU/L) ALT (IU/L) ALP (IU/L) Sham group 141 ± 26 43 ± 1 665 ± 94 Control group  589 ± 221  417 ± 185 2318 ± 583 Comparative  916 ± 146  527 ± 118 2042 ± 235 Example Example 3440 309 ± 37 155 ± 38 1614 ± 189 (1 mg/kg) Example 3605  487 ± 382  258 ± 219 1489 ± 533 (1 mg/kg) Example 3448  352 ± 210 181 ± 79 1148 ± 332 (1 mg/kg) Sham group 128 ± 18 48 ± 5 630 ± 87 Control group  643 ± 125  384 ± 156 2204 ± 327 Example 3696 325 ± 87 191 ± 21 1209 ± 125 (1 mg/kg) Example 3713 280 ± 61 163 ± 96 1008 ± 289 (1 mg/kg) Example 3747 245 ± 81 146 ± 70  960 ± 259 (1 mg/kg) Example 3752 358 ± 87 165 ± 47 1112 ± 184 (1 mg/kg) Example 5408 198 ± 65 197 ± 45 1005 ± 102 (1 mg/kg) (For all the cases, N = 8, average ± standard error) In comparative example, 25 mg/kg of cholestyramine was administered. In the case of the compounds of examples, aqueous solution of 1% HCO60 was used as a solvent.

TABLE 10 (Protocol B) Compound of Example AST (IU/L) ALT (IU/L) ALP (IU/L) (Pre-administration 102 ± 5  38 ± 5 508 ± 54 value) value) Control group 157 ± 35  82 ± 17 593 ± 77 Comparative 149 ± 10 70 ± 6 602 ± 78 Example 1 Comparative 109 ± 11 62 ± 9 453 ± 58 Example 2 Example 1 100 ± 2  53 ± 6 453 ± 50 (0.1 mg/kg) (For all the cases, N = 8, average ± standard error) In Comparative Example 1, 25 mg/kg of cholestyramine and in Comparative Example 2, 50 mg/kg of ursodeoxycholic acid was administered. Distilled water was used as a solvent.

[Test Example 6]

Obesity and fatty liver model

The obesity and fatty liver model in this test example was handled by referring to the method described in WO02/09757.

That is, 10 weeks old KKA^(y)/Ta Jcl male mice were used as obese mice (N=from 4 to 7). The test compounds dissolved or suspended in an aqueous solution of 1% HCO60 (manufactured by NIPPON CHEMICALS COMPANY, LTD.) and an aqueous solution of 1% HCO60 (manufactured by NIPPON CHEMICALS COMPANY, LTD.) as a control group were administered once a day for 2 weeks continuously. The weights of the mice were measured every day and compared with the weights measured on the day before the administration. On the day next to the final day of administration of the drug, the livers were extracted and concentrations of triglycerides in the liver tissues were measured by using a measurement kit (TRIGLYCERIDE TEST WAKO, manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.). The results are shown in Table 11 below.

It has been verified that the compounds of the present invention exhibit a body weight suppressing effect and a liver triglyceride lowering effect in obese mice, so that the compounds of the present invention have proved to be useful as drugs for the treatment and prevention of obesity and fatty liver. Moreover, it has also been verified that the compounds of other examples of the present invention not shown in Table 11 have excellent body weight suppressing effects and excellent triglyceride reduction effects.

TABLE 11 Body Weight (g) Liver Compound of Before 2 weeks Variation triglyceride Example administration later amount (mg/g) Control group 42.8 ± 0.4 42.0 ± 0.7 −0.8 ± 0.5 94 ± 18 (N = 7) Example 1 43.0 ± 0.5 41.0 ± 0.6 −1.9 ± 0.3 71 ± 13 (N = 7) (1 mg/kg) Example 3605 42.9 ± 1.1 41.4 ± 1.0 −1.5 ± 0.4 65 ± 7  (N = 4) (1 mg/kg) Control group 44.1 ± 0.6 44.8 ± 0.9 −0.7 ± 0.4 103 ± 19  (N = 7) Example 3713 44.0 ± 1.1 41.5 ± 2.4 −2.5 ± 0.6 59 ± 33 (N = 4) (1 mg/kg) Example 3747 44.3 ± 0.8 42.2 ± 1.8 −2.1 ± 1.0 47 ± 23 (N = 4) (1 mg/kg) Example 3752 43.8 ± 1.2 41.5 ± 1.0 −2.3 ± 0.9 56 ± 23 (N = 4) (1 mg/kg) Example 5408 44.0 ± 0.9 42.2 ± 1.6 −1.8 ± 0.5 70 ± 11 (N = 4) (1 mg/kg) Example 3696 43.5 ± 1.3 42.2 ± 2.2 −1.3 ± 0.3 76 ± 12 (N = 4) (1 mg/kg) Example 3440 44.6 ± 0.8 43.9 ± 1.8 −0.7 ± 1.0 88 ± 6  (N = 4) (1 mg/kg) Example 3448 44.1 ± 0.7 42.1 ± 3.2 −2.0 ± 0.7 74 ± 8  (N = 4) (1 mg/kg) (average ± standard error)

[Test Example 7]

In vitro assay of compounds inhibiting ileal bile acid transporter (IBAT) using Caco-2 cells

In this test example, the in vitro assay of compounds inhibiting ileal bile acid transporter using Caco-2 cells was carried out according to the Test Example 1 described in WO00/35889.

That is, 1×10⁵ cells/well Caco-2 cells were inoculated on a 24-well cell plate. For the assay, cells cultured for 14 days or more were used and the following procedure was followed. The cells were washed once with an assay buffer, Hank's buffer solution containing 25 mM glucose and 10 mM HEPES (pH 7.4), and then the buffer was replaced by an assay buffer to which the test compound was added. After adding [³H] taurocholate (trade name: NET-322, manufactured by DAIICHI CHEMICAL CO., LTD.) to a final concentration of 8 μM, the cells were incubated at 37° C for 30 minutes to allow [³H] taurocholate to be incorporated in Caco-2 cells by IBAT. The reaction was stopped by washing twice with a buffer prepared by adding 1mM taurocholate (trade name: T-4009, manufactured by SIGMA CHEMICAL COMPANY) to the assay buffer and lyzing the cells with 0.2 M NaOH. Measurement of the radioactivity was carried out by introducing the cell lyzate in 4 ml of liquid scintillation cocktail (trade name: Clearzol 1, manufactured by NACALAITESC), stirring the mixture well, and then measuring the radioactivity on a liquid scintillation counter (manufactured by PACKARD CO., LTD.). The inhibition rate (%) was determined from the radioactivity of a control which did not use the test compound and the radioactivity when the test compound having a fixed concentration was used and the concentration of the test compound at which 50% of the IBAT activity was inhibited was determined. This method has verified that the compounds of the present invention have potent inhibiting activity against IBAT, so that the compounds of the present invention have proven to be useful as drugs for the treatment and prevention of hyperlipidemia.

[Test Example 8]

In vitro assay of compounds which inhibit temporarily expressed human IBAT transporter or rat IBAT transporter using Cos 7 cells

In this test example, the in vitro assay of the compounds which inhibit temporarily expressed human IBAT transporter or rat IBAT transporter using Cos cells was carried out according to the method described in Am. J. Physiol., 274, G157-169.

That is, 2.5×10⁻⁵ cells/well Cos 7 were inoculated on a 24-well cell plate. One day later, 0.3 μg per well of cDNA of a human IBAT or a rat IBAT was transfected by using FuGENE6 (manufactured by ROCHE PHARMACEUTICAL CO., LTD.). For the assay, the cells cultured for one day after the transfection were used and the following procedure was followed. The cells were washed once with an assay buffer, Hank's buffer solution containing 25 mM glucose and with 10 mM HEPES (pH 7.4), and then the assay buffer was replaced by an assay buffer to which the test compound was added. After adding [³H] taurocholate to a final concentration of 8 μM, the cells were incubated at 37° C for 60 minutes. [³H] taurocholate was allowed to be incorporated in Cos 7 cells through human IBAT or rat IBAT. The reaction was stopped by washing twice with a buffer prepared by adding 1mM taurocholate to the assay buffer and lyzing the cells with 0.2M NaOH. Measurement of radioactivity was carried out by introducing the cell lyzate in 4 ml of liquid scintillation cocktail, stirring the mixture well, and then measuring the radioactivity by a scintillation counter. The inhibition rate (%) was determined from the radioactivity of a control which did not use the test compound and the radioactivity when the test compound having a fixed concentration was used. The concentration of the test compound at which 50% of human IBAT activity or rat IBAT activity was inhibited was determined.

The results are shown in Table 12 below. It has been verified that the compounds of the present invention have potent inhibitory activity against human BAT and rat IBAT. Therefore, the compounds of the present invention have proven to be useful as drugs for the treatment and prevention of hyperlipidemia. Moreover, it has also been verified that the compounds of other examples of the present invention not shown in Table 12 have potent inhibition activity against human IBAT and rat IBAT.

TABLE 12 Cos 7 human IBAT Cos 7 rat IBAT Compound of Example IC₅₀ (μM) IC₅₀ (μM) Comparative Example* 10 0.2 Example 3835 0.043 Not tested Example 1 0.025 0.007 Example 3932 0.036 0.009 Example 9 0.076 0.036 Example 425 0.17 Not tested Example 801 0.1 Not tested Example 1056 0.1 Not tested Example 1178 0.093 Not tested Example 1433 0.103 Not tested Example 1555 0.153 Not tested Example 1810 0.167 Not tested Example 3440 0.037 0.010 Example 3695 0.037 0.005 Example 969 0.1 Not tested Example 968 0.038 Not tested Example 593 0.092 Not tested Example 592 0.1 Not tested Example 3853 0.028 0.009 Example 3607 0.041 Not tested Example 3608 0.059 Not tested Example 4512 0.063 Not tested Example 4424 0.091 Not tested Example 4425 0.089 Not tested Example 4905 0.1 Not tested Example 1069 0.1 Not tested Example 867 0.1 Not tested Example 3708 0.07 Not tested Example 3506 0.127 Not tested Example 3696 0.039 Not tested Example 3605 0.039 Not tested Example 3475 0.1 Not tested Example 3558 0.07 Not tested Example 3448 0.037 Not tested Example 3572 0.1 Not tested Example 3593 0.07 Not tested Example 3554 0.065 Not tested Example 3698 0.072 Not tested Example 4210 0.1 Not tested Example 3409 0.045 Not tested Example 3433 0.055 Not tested Example 3449 0.055 Not tested Example 3441 0.085 Not tested Example 3444 0.1 Not tested Example 3567 0.1 Not tested Example 3662 0.1 Not tested Example 3709 0.049 Not tested Example 3717 0.03 Not tested Example 3722 0.039 Not tested Example 3725 0.052 Not tested Example 3783 0.048 Not tested Example 3429 0.055 Not tested Example 3568 0.094 Not tested Example 3587 0.07 Not tested Example 3705 0.054 Not tested Example 3724 0.069 Not tested Example 3764 0.08 Not tested Example 3723 0.025 Not tested Example 3768 0.072 Not tested Example 3770 0.057 Not tested Example 3774 0.1 Not tested Example 3454 0.068 Not tested Example 3544 0.1 Not tested Example 3599 0.054 Not tested Example 3604 0.045 Not tested Example 3697 0.069 Not tested Example 4226 0.099 Not tested Example 4250 0.1 Not tested Example 4266 0.1 Not tested Example 4258 0.1 Not tested Example 4261 0.1 Not tested Example 4232 0.099 Not tested Example 4248 0.1 Not tested Example 4384 0.1 Not tested Example 4405 0.062 Not tested Example 4456 0.1 Not tested Example 4458 0.1 Not tested Example 4479 0.078 Not tested Example 4526 0.1 Not tested Example 4534 0.076 Not tested Example 4539 0.064 Not tested Example 4600 0.078 Not tested Example 3414 0.088 Not tested Example 3410 0.068 Not tested Example 3710 0.052 Not tested Example 3714 0.058 Not tested Example 3719 0.1 Not tested Example 3412 0.075 Not tested Example 3434 0.071 Not tested Example 3426 0.058 Not tested Example 3713 0.037 Not tested Example 3729 0.088 Not tested Example 3413 0.073 Not tested Example 3416 0.1 Not tested Example 3711 0.063 Not tested Example 3716 0.089 Not tested Example 3727 0.066 Not tested Example 3726 0.073 Not tested Example 3730 0.084 Not tested Example 3765 0.1 Not tested Example 3772 0.089 Not tested Example 3854 0.028 Not tested Example 4233 0.046 Not tested Example 4259 0.067 Not tested Example 4408 0.073 Not tested Example 4412 0.1 Not tested Example 4528 0.091 Not tested Example 4543 0.082 Not tested Example 4547 0.072 Not tested Example 4589 0.046 Not tested Example 4402 0.043 Not tested Example 4613 0.1 Not tested Example 4246 0.072 Not tested Example 4263 0.072 Not tested Example 4258 0.074 Not tested Example 4268 0.1 Not tested Example 4247 0.091 Not tested Example 4234 0.1 Not tested Example 4385 0.1 Not tested Example 4460 0.1 Not tested Example 4522 0.097 Not tested Example 4527 0.073 Not tested Example 4531 0.1 Not tested Example 4581 0.1 Not tested Example 4540 0.1 Not tested Example 4585 0.078 Not tested Example 4587 0.060 Not tested Example 4251 0.1 Not tested Example 4371 0.074 Not tested Example 4260 0.074 Not tested Example 4243 0.078 Not tested Example 4236 0.10 Not tested Example 4513 0.092 Not tested Example 4546 0.087 Not tested Example 4401 0.061 Not tested Example 4605 0.079 Not tested Example 4448 0.10 Not tested Example 3733 0.057 Not tested Example 3736 0.05 Not tested Example 3747 0.045 Not tested Example 3748 0.081 Not tested Example 3750 0.075 Not tested Example 3752 0.041 Not tested Example 3754 0.092 Not tested Example 5043 0.062 Not tested Example 5298 0.076 Not tested Example 4551 0.076 Not tested Example 5416 0.077 Not tested Example 5417 0.026 Not tested Example 5407 0.052 Not tested Example 5408 0.032 Not tested Example 5409 0.042 Not tested Example 4221 0.043 Not tested Example 4223 0.025 Not tested Example 5410 0.1 Not tested Example 5411 0.097 Not tested Example 5412 0.037 Not tested Example 5418 0.069 Not tested Example 5419 0.039 Not tested Example 5420 0.068 Not tested Example 5413 0.065 Not tested Example 5414 0.1 Not tested Example 5415 0.44 Not tested *In Comparative Example, the compound specifically described in Synthesis Example 1 of WO93/16055: (−)-trans-3-butyl-3-ethyl-2,3,4,5-tetrahydro-5-phenyl-1,4-benzothio-azepine-1,1-dioxide was used.

[Test Example 9]

In vitro assay of compounds inhibiting temporarily expressed human IBAT transporter in which alanine 171 was substituted by serine using Cos 7 cells

The in vitro assay of the compounds inhibiting temporarily expressed human BAT transporter in which alanine 171 was substituted by serine was carried out in the same manner as in Test Example 4 except for using the cDNA of IBAT in which alanine 171 was substituted by serine in the human IBAT amino acid sequence.

Note that actually in the case of humans, the proportion of individuals having the IBAT transporter in which alanine 171 has been substituted by serine is said to be 28% [J. Clin. Invest., 1997, 99, 1880-1887].

The results are shown in Table 13 below. The value is a rate of inhibition (%) of the radioactivity of the test compound at a test compound concentration of 10 nM with respect to the radioactivity of the control without the test compound. It has been verified that the compound of the present invention has a potent inhibiting activity on the human IBAT in which alanine 171 is substituted by serine which is equivalent to that of the human IBAT in which alanine 171 is not substituted by serine. Therefore, the compound has proven to be useful as a drug for the treatment and prevention of hyperlipidemia. Moreover, it has been verified that the compounds of other examples of the present invention not shown in Table 13 have inhibitory effect against the human IBAT in which alanine 171 is substituted by serine.

TABLE 13 Cos 7, human IBAT in which alanine 171 is substituted by serine; Rate of inhibition (%) at a test Compound of Example compound concentration of 10 nM Example 1 53

[Test Example 10]

In vitro assay of effects of compounds on Na⁺ dependent amino acid transporter and Na⁺ dependent water-soluble vitamin transporter using Cos 7 cells

In this test example, the in vitro assays of the compound on various transporters using Cos 7 cells were carried out according to the method described in Published Translation of Japanese Patent Application No. 10-503830.

That is, 2.5×10⁻⁵ cells/well of Cos 7 cells were inoculated on a 24-well cell plate. Two days later, the cells were washed once with an assay buffer, Hank's buffer solution containing 25 mM glucose and with 10 mM HEPES (ph 7.4), and then the buffer was replaced by an assay buffer to which the test compound was added. After adding to this, [³H] alanine (trade name; NET-348, manufactured by DAIICHI CHEMICAL CO., LTD.), [³H] leucine (trade name: NET-460, manufactured by DAIICHI CHEMICAL CO., LTD.), [³H] phenylalanine (trade name: MT903, MORAVEK), [³H] methionine (trade name: MT862, MORAVEK), [³H] lysine (trade name: MT909, MORAKEK), or [³H]choline (trade name: TRK593, AMERSHAM BIOSCIENCES CO., LTD.) to a final concentration of 8 μM, the mixture was incubated at 37° C for 60 minutes to allow Cos 7 cells to incorporate them. The reaction was stopped by washing the cells twice with the assay buffer and then lyzing them with 0.2 M NaOH. Measurement of the radioactivity was carried out by introducing the lyzate in 4 ml of liquid scintillation cocktail, stirring the mixture well, and then measuring on a liquid scintillation counter. The inhibition rate (%) was determined from the radioactivity of a control without test compounds and the radioactivity when the test compound having a fixed concentration was used, and then the concentration of the test compound at which 50% of the transporter activity was inhibited was determined.

In the small intestine epithelial cells having IBAT therein, there are also Na⁺ dependent transporters, which further include an amino acid transporter and a water-soluble vitamin transporter. Essential amino acids are indispensable for normal growth and healthy life support [TOKYO KAGAKU DOZIN CO., LTD., 2nd edition of SEIKAGAKU JITEN (Dictionary of Biochemistry), P1052]. Choline is a water-soluble vitamin, deficiency of which in human body causes fatty liver and hepatocirrhosis [TOKYO KAGAKU DOZIN CO., LTD., 2nd edition, SEIKAGAKU JITEN (Dictionary of Biochemistry), P1050].

The results are shown in Table 14. It has been verified that the compound of the present invention has significant inhibitory specificity against human IBAT and rat IBAT and it has been shown that the compound of the present invention can serve as a drug for the treatment and prevention of hyperlipidemia. Similar effects were obtained for other amino acids, such as leucine, phenylalanine, methionine, and lysine, and even choline, which is a water-soluble vitamin. Moreover, it has also been verified that compounds of other examples of the present invention not shown in Table 14 have significant inhibitory specificities against human IBAT and rat IBAT.

TABLE 14 Compound of Example IC₅₀ (μM) against alanine transporter Example 1 33

[Test Example 11]

Microbial mutagenicity (Ames test)

In this test example, the microbial mutagenicity test was carried out according to Ames Salmonella Mutation Assay.

[0533]

The strains used are Salmonella typhimurium TA98 and Salmonella typhimurium TA100 strains. In an L-shaped tube containing a sterilized preculture medium (trade name: Nutrient Broth No. 2, manufactured by KANTO KAGAKU) was added a loopful of Salmonella typhimurium TA98 or Salmonella typhimurium TA100, which then was cultured in a shaking incubator at 37° C, for 8 hours with 100 shakes per minute. 0.1 ml of this microbial culture broth was added to 2 ml of sterilized soft agar warmed at 45° C, containing 0.05 mM of L - histidine and 0.05 mM (+)-biotin. After stirring, the mixture was spread on a minimum glucos agar plate medium (trade name: TESMEDIA AN, manufactured by ORIENTAL YEAST CO., LTD.) in a Petri dish and allowed to solidify. A circular filter paper was made by punching a filter paper (trade name: Quantitative Ashless No. 7, manufactured by ADVANTECH COMPANY, LTD.), sterilized, and disposed on the solidified agar. Then, 1 μl of the test compound having a concentration of 10 mM was put on the filter paper and culturing was performed at 37° C for 48 hours. For the judgment of the microbial mutagenicity, the occurrence of a mutant colony centered on the filter paper where the test compound was diffused was judged as positive and no occurrence of mutant colonies in that area was judged as negative.

As a result, it has been verified that all the compounds of the examples of the present invention were negative on both TA98 and TA100 in the microbial mutagenicity test (Ames test) and have no mutagenicity. Thus, the compounds of the present invention have proven to be safe. Therefore, it has been indicated that the compounds of the present invention can be drugs for the treatment and prevention of hyperlipidemia.

[Test Example 12]

Toxicity with respect to alimentary canal

To evaluate the toxicity of the compounds of the present invention to the alimentary canal, the cytotoxicity to Caco 2, which is a human originated small intestine epithelial cell line, was tested by referring to the method of Bestwick CS et al. [Biochimica et Biophysica Acta 1474: 47-55, 1999].

That is, Caco 2 cells (purchased from ATCC) were inoculated on a 96-well plate such that there were 10,000 cells/well [MEM-E medium, 10% FBS (Fetal Bovine Serum), 1% NEAA (Non Essential Amino Acid) solution, (both manufactured by GIBCO PHARMACEUTICAL COMPANY)]. After culturing for 48 hours, the test compounds were diluted with the culture medium and added to the respective wells. After 2 hours, 50 μl of the culture broth was collected and the LDH activity in the collected culture broth was measured by using an LDH activity measuring kit (CytoTox 96 Non-Radioactive Cytotoxicity Assay, manufactured by PROMEGA CORPORATION). Relative activities were calculated assuming the LDH activity as 100% when the Caco 2 cells were treated with the cytolytic agent and the obtained relative activities were taken as cytotoxicities to Caco 2 cell.

The results are shown in Table 15 below. From the results, it is apparent that the compounds of the present invention have low cytotoxicity or no cytotoxicity to Caco 2 cells and that the compounds of the present invention have very little toxicity or no toxicity to the alimentary canal. Note that the IBAT inhibiting agent having a structure of quaternary ammonium salt used as a control to the present invention (compound 5 (Synthesis Example 19) having the highest activity among the compounds specifically described in WO02/08211: 1-{4-[4-(3,3-dibutyl-7-dimethyl-amino-1,1-dioxo-2,3,4,5-tetrahydro-1,4- benzothiazepin-5-yl)phenoxy-methyl]benzyl}-4-aza-1-azoniabycyclo- [2.2.2]octane chloride (the compound A mentioned later)) showed cytotoxicity to small intestine epithelial cell line at low concentrations and thus has toxicity to alimentary canal. In contrast, it has been verified that the compounds of the present invention have little toxicity or no toxicity to the alimentary canal, or are less toxic, so that they are more preferable as pharmaceuticals.

TABLE 15 Toxicity (%) to Caco 2 Compound of Example 30 μM 10 μM 3 μM Comparative Example* 79 22 1.5 Example 3853 <1 <1 <1 Example 3605 <1 <1 <1 Example 3835 <1 <1 <1 Example 3440 <1 <1 <1 Example 3695 <1 <1 <1 Example 3607 <1 <1 <1 Example 3608 <1 <1 <1 Example 3696 <1 <1 <1 Example 3448 <1 <1 <1 Example 3409 <1 <1 <1 Example 3709 <1 <1 <1 Example 3783 <1 <1 <1 Example 3723 <1 <1 <1 Example 3710 <1 <1 <1 Example 3713 <1 <1 <1 Example 3759 <1 <1 <1 Example 5043 <1 <1 <1 Example 5298 <1 <1 <1 Example 5480 <1 <1 <1 Example 5735 <1 <1 <1 Example 5856 <1 <1 <1 Example 5857 <1 <1 <1 Example 3705 <1 <1 <1 Example 3747 <1 <1 <1 Example 3752 <1 <1 <1 Example 5408 <1 <1 <1 *In Comparative Example, the compound 5 (Synthesis Example 19) having the highest activity among the compounds specifically described in WO02/08211: 1-{4-[4-(3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)-phenoxymethyl]benzyl}-4-aza-1-azoniabicyclo-[2.2.2]octane chloride (compound A mentioned later) was used.

[Test example 13]

“Cholestasis-caused hepatopathy” model (bile duct partial ligation model)

In this test example, the model of cholestasis-caused hepatopathy was tested according to the method described in Test Example 5.

That is, the abdomens of 8 to 10 weeks old SD (IGS) male rats were cut open under anesthesia with pentobarbital and partial ligation surgery of the bile duct was carried out. After the surgery, 200 mg/kg of bile acid and an BAT inhibiting compound were forcibly orally administered to the rats (each n=3). As a control group, physiological saline (n=6) was administered (n=3). To observe the effect of the partial ligation surgery, a sham group (the abdomen was cut open under anesthesia with pentobarbital but partial ligation surgery of the bile duct was not carried out) and an untreated group were established (each n=3). After 24 hours-from the administration a blood sample was taken from the abdominal aorta and AST, ALT, and ALP in the blood were measured using the method described in Test Example 5.

The results are shown in Tables 16 and 17 below. It has been verified that the IBAT inhibiting compounds inhibit the rise in AST, ALT, and ALP caused by partial ligation of the liver and have ameliorating effects on cholestasis-caused hepatopathy. Therefore, it has been indicated that the compounds are useful as drugs for the treatment and prevention of cholestasis-caused hepatopathy, in particular as drugs for the treatment and prevention of primary biliary cirrhosis and primary sclerosing cholangitis. Moreover, it has also been verified that compounds of other examples of the present invention not shown in Table 16, can be expected to have excellent ameliorating effects on cholestasis-caused hepatopathy.

TABLE 16 Compound of Example AST (IU/L) ALT (IU/L) ALP (IU/L) Untreated group 119 ± 2  35 ± 2 769 ± 149 Sham group 174 ± 5  41 ± 3 567 ± 44  Control group 509 ± 86 245 ± 48 1135 ± 125  Compound C 313 ± 82 113 ± 44 948 ± 208 (10 mg/kg) Compound D 275 ± 12  73 ± 17 715 ± 24  (10 mg/kg) (For all the cases, N = 3, average ± standard error)

TABLE 17 Compound of Example AST (IU/L) ALT (IU/L) ALP (IU/L) Sham group 141 ± 26 43 ± 1  665 ± 94 Control group  589 ± 221 417 ± 185 2318 ± 583 Comparative  916 ± 146 527 ± 118 2042 ± 235 Example Compound A  547 ± 159 281 ± 103 1266 ± 160 (10 mg/kg) Compound B 261 ± 63 138 ± 54  1335 ± 116 (1 mg/kg) Compound E 280 ± 72 180 ± 68  1345 ± 145 (10 mg/kg) Compound F 320 ± 66 214 ± 53  1423 ± 115 (10 mg/kg) (For all the cases, N = 3, average ± standard error) In Comparative Example, 25 mg/kg of cholestyramine was administered.

[Test Example 14]

“Cholestasis-caused hepatopathy” model (bile acid loaded model)

In this test example, the model of hepatopathy due to loading of bile acid was carried out similarly to the protocol B in Test Example 5. However, the administration period in this test example was changed to 4.5 days. The results are shown in Tables 18 and 19 below. It has been verified that the IBAT inhibiting compounds inhibit the rise in AST and ALT caused by the loading of bile acid and have an ameliorating effect on cholestasis-caused hepatopathy. Therefore, the compounds have proven to be useful as drugs for the treatment and prevention of cholestasis-caused hepatopathy, in particular as drugs for the treatment and prevention of primary biliary cirrhosis and primary sclerosing cholangitis. Moreover, the compounds of other examples of the present invention not shown in Tables 18 and 19 can be expected to have excellent ameliorating effects on cholestasis-caused hepatopathy.

TABLE 18 Compound of Example AST (IU/L) ALT (IU/L) (Pre-administration value) 108 ± 6  38 ± 2 Control group 157 ± 35  82 ± 17 Comparative Example 1 149 ± 10 70 ± 6 Comparative Example 2 109 ± 11 62 ± 9 Compound C (10 mg/kg) 100 ± 2  53 ± 6 Compound D (10 mg/kg) 100 ± 9  46 ± 4 (For all the examples, N = 6, average ± standard error) In Comparative Example 1, 25 mg/kg of cholestyramine was administered and in Comparative Example 2, 50 mg/kg of ursodeoxycholic acid was administered.

TABLE 19 Compound of Example AST (IU/L) ALT (IU/L) Untreated group 97 ± 5 36 ± 3 Control group 156 ± 14 76 ± 8 Compound B (0.1 mg/kg) 110 ± 4  54 ± 6 Compound E (10 mg/kg) 105 ± 11 46 ± 3 Compound F (10 mg/kg) 123 ± 16 58 ± 5 (For all the cases, N = 6, average standard error)

Note that the IBAT inhibitors and production methods therefor used in the test examples are as follows.

Compound A; a compound having the following structure and chemical name

Chemical name: 1-{4-[4-(3,3-Dibutyl-7-dimethylamino-1,1-dioxo- 2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenoxymethyl]benzyl}-4- aza-1-azoniabicyclo[2.2.2]octane chloride (manufactured according to the method described in WO02/08211)

Compound B; a compound having the following structure and chemical name

Chemical name: Trans-3-butyl-3-ethyl-2,3,4,5-tetrahydro-7,8- dimethoxy-5-phenyl-1,4-benzothiazepine-1,1-dioxide (manufactured according to the method described in Published Translation of Patent Application No. Hei10-504035)

Compound C; a compound having the following structure and chemical name

Chemical name: Trans-3-butyl-3-ethyl-2,3,4,5-tetrahydro-5- phenyl-1,4-benzothiazepine-1,1-dioxide (manufactured according to the method described in WO93/16055)

Compound D; a compound having the following structure and chemical name

Chemical name: Cis-[3-(3,3-dibutyl-7-dimethylamino-4-hydroxy- 1,1-dioxo-2,3,4,5-tetrahydro-1-benzothiepin-5-yl)phenyl]trimethyl- ammonium iodide (manufactured according to the method described in Published Translation of Patent Application No. 2001-526627)

Compound E; a compound having the following structure and chemical name

Chemical name: Methyl 1-(3,4-dimethoxyphenyl)-3- (3-ethylvaleryl)-4-hydroxy-6,7,8-trimethoxy-2-naphthoate (manufactured according to the method described in Japanese Patent No. 2839805)

Compound F; a compound having the following structure and chemical name

Chemical name: {1-O-[4-(3,4-dimethoxyphenyl)-2-(3-ethyl- pentanoyl)-5,6,7-trimethoxy-3-(methoxycarbonyl)naphthalen-1-yl]- β-D-glucopyranosido}uronic acid (manufactured according to the method described in Japanese Patent Application No. Hei 9-241206).

[Test Example 15]

Steatohepatitis model

In this test example, the steatohepatitis model was examined referring to the method of Okan A., et al. (Dig Dis Sci 47:2389-2397, 2002).

That is, 7 weeks old Wistar rats were fed with a choline-deficient diet (manufactured by Oriental Yeast Co., Ltd.) for 2 weeks to prepare a steatohepatitis model. A suspension of a test compound in an aqueous solution of 0.5% methyl cellulose (manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.) and an aqueous solution of 0.5% methyl cellulose (manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.) as a control were orally administered once a day for consecutive 2 weeks. On the day next to the last day of administration, a blood sample was taken from the abdominal aorta and AST (GOT) and ALT (GPT) in the blood were measured by using measuring kits (GOTII-HA TEST WAKO and GPTII-HA TEST WAKO, respectively, the both were manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.) on an auto analyzer (NITTECH ANALYZER SUPER Z818). The results are shown in Table 20 below. It has been verified that the compounds of the present invention exhibit blood AST and ALT level-decreasing effects on steatohepatitis model rats, so that it has been shown that the compounds of the present invention are useful for the treatment and prevention of steatohepatitis. Moreover, it has also been verified that the compounds of other examples of the present invention not shown in Table 20 have excellent AST and ALT level-decreasing effects.

TABLE 20 Compound of Example AST (IU/L) ALT (IU/L) Control group (n = 6) 180 ± 46  245 ± 57 Example 3713 (3 mg/kg, n = 4) 77 ± 37 118 ± 36 Example 3747 (3 mg/kg, n = 4) 63 ± 86 102 ± 50 Example 3752 (3 mg/kg, n = 4) 69 ± 98  88 ± 45 Example 5408 (3 mg/kg, n = 4) 103 ± 45  149 ± 38 Example 3696 (3 mg/kg, n = 4) 98 ± 23 145 ± 34 Example 3440 (3 mg/kg, n = 4) 125 ± 34  167 ± 93 Example 3448 (3 mg/kg, n = 4) 134 ± 23  143 ± 79 Example 3605 (3 mg/kg, n = 4) 80 ± 34 121 ± 36 (Average ± standard error)

Although the invention has been described with respect to a specific embodiment for a complete and clear disclosure, the appended claims are not to be thus limited but are to be construed as embodying all modifications and alternative constructions which may occur to one skilled in the art which fairly fall within the basic teaching herein set forth. 

1. A compound represented by formula (1) below

wherein R¹ and R², which may be mutually different, each represents an alkyl group having from 1 to 10 carbon atoms; m represents an integer of 1 or 2, and R³ and R⁴, which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms; Y represents any one of —NHCS—, —NHCSNH—, and —NHCSO— where the —NH in the —NHCS— represents a bond which links with an adjacent benzene ring and the CS— in the —NHCS— represents a bond which links with an adjacent Z, and the —NH in the —NHCSO— represents a bond which links with an adjacent benzene ring and the CSO— in the —NHCSO— represents a bond which links with an adjacent Z; Z— (N⁺R⁵R⁶R⁷)_(n) represents an alkyl group having from 2 to 10 carbon atoms or an alkenyl group having from 2 to 10 carbon atoms which is substituted with n (−N⁺R⁵R⁶R⁷)s, where at least one of methylenes which constitute Z may be replaced by any one of a phenylene and an —O—; n is an integer of 1 or 2; and N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent I) R⁵, R⁶, and R⁷, which may be mutually different, each represents any one of an alkyl group having from 1 to 10 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, and an alkynyl group having from 2 to 10 carbon atoms, where the alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, an —SO₃H group, and further, at least one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰— where R⁸ represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms and the alkyl group and alkenyl group represented by R may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group; R⁹ and R^(10,) which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms or alkenyl group having from 2 to 5 carbon atoms and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group; and W⁻ represents a counter anion, II) N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring which is formed by 4 to 9 carbon atoms in addition to an ammonium nitrogen atom, provided that the position of its bonding with Z is the ammonium nitrogen atom, where one of the carbon atoms which constitute the ring in the monocyclic ring and the bicyclic ring may be replaced by any one atom of oxygen, nitrogen, and sulfur, and moreover, the monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a thioxo group, a cyano group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a carboxyl group, a —CONH₂ group, an —SO₃H group, and an R¹¹ group; R¹¹ represents an alkyl group having from 1 to 8 carbon atoms or an alkenyl group having from 2 to 8 carbon atoms, where the alkyl group and the alkenyl group represented by R¹¹ may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group; moreover, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—-, a —CO₂ —, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—, where R⁸, R⁹, R¹⁰, and W⁻ are as described above; among R⁵, R⁶, and R⁷, a group which is not involved in formation of the monocyclic ring and the bicyclic ring is the same as that in I) described above, III) N⁺R⁵R⁶R⁷ represents a pyridinium ring, a quinolinium ring, or an isoquinolinium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the pyridinium ring, the quinolinium ring, and the isoquinolinium ring may be substituted with at least one of a cyano group, a nitro group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, an alkoxy group having from 1 to 5 carbon atoms, a carboxyl group, a —CONH₂ group, an —SO₃H group, and an —R¹² group; R¹² represents an alkyl group having from 1 to 9 carbon atoms or an alkenyl group having from 2 to 9 carbon atoms; and the alkyl group and the alkenyl group represented by R¹² may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group; and further, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—, where R⁸, R⁹, R¹⁰, and W⁻ are as described above, and X represents a counter anion.
 2. The compound according to claim 1, wherein the Z-(N⁺R⁵R⁶R⁷)_(n) represents an alkyl group having from 2 to 10 carbon atoms which is substituted with n (—N⁺R⁵R⁶R⁷)s and at least one of methylenes which constitute Z may be replaced by any one of a phenylene and an —O—.
 3. The compound according to claim 2, wherein the Z-(N⁺R⁵R⁶R⁷)_(n) represents a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one —N⁺R⁵R⁶R⁷ and at least one of methylenes which constitute Z may be replaced by any one of a phenylene and an —O—.
 4. The compound according to claim 3, wherein the Z-(N⁺R⁵R⁶R⁷)_(n) represents a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one —N⁺R⁵R⁶R⁷, a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one —N⁺R⁵R⁶R⁷ and one of methylenes which constitute Z is replaced by a phenylene, a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one —N⁺R⁵R⁶R⁷ and one of methylenes which constitute Z is replaced by an —O—, or a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one —N⁺R⁵R⁶R⁷ and one of methylenes which constitute Z is replaced by a phenylene and another of methylenes which constitute Z is replaced by an —O—.
 5. The compound according to claim 4, wherein Z represents a straight chain methylene group having from 2 to 10 carbon atoms, a straight chain methylene group having from 2 to 10 carbon atoms of which one methylene is replaced by a phenylene, a straight chain methylene group having from 2 to 10 carbon atoms of which one methylene is replaced by an —O—, or a straight chain methylene group having from 2 to 10 carbon atoms of which one methylene is replaced by a phenylene and another methylene is replaced by an —O—.
 6. The compound according to claim 5, wherein Z represents a straight chain methylene group having from 2 to 10 carbon atoms.
 7. The compound according to claim 5, wherein Y represents —NHCS— or —NHCSNH— at the para- or meta-position.
 8. The compound according to claim 6, wherein Y represents —NHCS— or —NHCSNH— at the para- or meta-position.
 9. The compound according to claim 8, wherein Y represents —NHCSNH— at the meta-position; and Z represents a straight chain methylene group having from 2 to 10 carbon atoms.
 10. The compound according to claim 8, wherein Y represents —NHCS— at the meta-position; and Z represents a straight chain methylene group having from 2 to 10 carbon atoms.
 11. The compound according to claim 10, wherein Y represents —NHCS— at the meta-position; and Z represents a straight chain methylene group having 5 carbon atoms.
 12. The compound according to claim 5, wherein Y represents —NHCSNH— at the meta-position; and Z represents a straight chain methylene group having from 2 to 10 carbon atoms of which one methylene is replaced by a phenylene.
 13. The compound according to claim 7, wherein Y represents —NHCS— or —NHCSNH— at the meta-position; and Z is represented by formula (sp-14)

wherein *a is bonded to Y in the formula (1) and *b is bonded to N⁺R⁵R⁶R⁷.
 14. The compound according to claim 12, wherein Y represents —NHCSNH— at the meta-position; and Z is represented by formula (sp-14)

wherein *a is bonded to Y in the formula (1) and *b is bonded to N⁺R⁵R⁶R⁷.
 15. The compound according to claim 1, wherein N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent: I) R⁵, R⁶, and R⁷, which may be mutually different, each represents any one of an alkyl group having from 1 to 10 carbon atoms, an alkenyl group having from 3 to 8 carbon atoms, and an alkynyl group having from 3 to 9 carbon atoms, where the alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a thienyl group, a cyclohexyl group, a cyano group, a hydroxyl group, an oxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group, and further, at least one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a thienylene, a furylene, an —O—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N³⁰W⁻R⁹R¹⁰— where R⁸ represents an alkyl group having from 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms and the alkyl group may be substituted with at least one of a phenyl group and a hydroxyl group; R9 and R10, which may be mutually different, each represents an alkyl group having from 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms and the alkyl group may be substituted with at least one of a phenyl group and a hydroxyl group, II) N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring which is any one of a pyrrolidinium ring, a piperidinium ring, a morpholinium ring, a thiomorpholinium ring, a piperazinium ring, an azepanium ring, a quinuclidinium ring, and a 1,4- diazabicyclo[2.2.2]octanium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a cyano group, a phenyl group, a —CONH₂ group, and an —R¹¹ group; R¹¹ represents an alkyl group having from 1 to 6 carbon atoms or an alkenyl group having 3 carbon atoms, where the alkyl group represented by R¹¹ may be substituted with at least one of a hydroxyl group, a cyano group, a phenyl group, and a —CONH₂ group; moreover, at least one of methylenes which constitute the alkyl group may be replaced by any one of an —O—, a —CO₂—, and an —NHCO—; among R⁵, R⁶, and R⁷, a group which is not involved in formation of the ring represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, or an alkynyl group having 3 to 6 carbon atoms; the alkyl group, the alkenyl group, and the alkynyl group represented by R⁵, R⁶, or R⁷ may be substituted with at least one of a phenyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cyclopropyl group, a cyclopentyl group, a cyano group, a hydroxyl group, an oxo group, a nitro group, a carboxyl group, an —CONH₂ group, and an —SO₃H group; and moreover, at least one of methylenes which constitute the alkyl group may be replaced by any one of a phenylene, an —O—, and a —CO₂—, III) N⁺R⁵R⁶R⁷ represents a pyridinium ring, a quinolinium ring, or an isoquinolinium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the pyridinium ring and the quinolinium ring may be substituted with at least one of a cyano group, a nitro group, a phenyl group, a thienyl group, a pyridyl group, an alkoxy group having from 1 to 3 carbon atoms, a carboxyl group, a —CONH₂ group, and an —R¹² group; R¹² represents an alkyl group having from 1 to 9 carbon atoms or an alkenyl group having from 2 to 4 carbon atoms; and the alkyl group and the alkenyl group represented by R¹² may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a cyano group, a nitro group, a hydroxyl group, an oxo group, a carboxyl group, and an —SO₃H group; and further, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of an —S —, a —CO₂—, an —NHCO—, and an —NR⁸— where R⁸ represents an alkyl group having 1 to 3 carbon atoms and the alkyl group may be substituted with at least one hydroxyl group.
 16. The compound according to claim 1, wherein N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent: I) R⁵, R⁶, and R⁷, which may be mutually different, each represents a straight chain alkyl group having from 1 to 10 carbon atoms, a straight chain alkenyl group having from 3 to 6, or 8 carbon atoms, a branched alkenyl group having 4, 6, or 7 carbon atoms, a straight chain alkynyl group having from 3, 5, 6, 7, or 9 carbon atoms, or a branched alkynyl group having 6 carbon atoms, in which 1) the alkyl group, alkenyl group, and alkynyl group represented by R⁵, R⁶, and R⁷ are substituted with any one of a phenyl group, a thienyl group, a cyclohexyl group, a cyano group, a hydroxyl group, an oxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group, 2) the alkyl group, the alkenyl group, and the alkynyl group are substituted with two hydroxyl groups, 3) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group and one —SO₃H group, 4) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one oxo group and one phenyl group, 5) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group and two phenyl groups, 6) one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by any one of a phenylene, a furylene, a —CO₂—, an —NHCO—, an —NR⁸— (where R⁸ represents a methyl group, an ethyl group, an n-propyl group, a 2-propenyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, or a benzyl group), and an —N⁺W⁻R⁹R¹⁰— (where R⁹ and R¹⁰ each represents a methyl group, an ethyl group, an n-propyl group, a 2-propenyl group, a 2-hydroxyethyl group, or a benzyl group), 7) two of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group are replaced by any one selected from two (—O—)s, one phenylene and one —O—, one —O— and one —NR⁸—, and one —NHCO— and one —O—, 8) three of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group are replaced by any one selected from two (—O—)s and one —NR⁸—, or one phenylene and two (—NHCO—)s, 9) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by an —O—, 10) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by an —NR⁸—, 11) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group, and moreover one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by a furylene, 12) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one oxo group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by a thienylene, or 13) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one oxo group, and moreover, two of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group are replaced by one —O— and one phenylene, or the alkyl group, alkenyl group, and alkynyl group are neither substituted nor replaced, II) N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring which is any one of a pyrrolidinium ring, a piperidinium ring, a morpholinium ring, a thiomorpholinium ring, a piperazinium ring, an azepanium ring, a quinuclidinium ring, and a 1,4- diazabicyclo[2.2.2]octanium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the monocyclic ring and the bicyclic ring are 1) substituted with any one of a hydroxyl group, an oxo group, a cyano group, a phenyl group, a —CONH₂ group, and an —R¹¹ group, 2) substituted with one cyano group and one hydroxyl group, 3) substituted with one hydroxyl group and one —R¹¹,4) substituted with one oxo group and one —R¹¹, 5) substituted with two oxo groups, or 6) substituted with two (—R¹¹)s, or the monocyclic ring and the bicyclic ring are unsubstituted, where R¹¹ represents any one of a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-propenyl group, a benzyl group, an acetylamino group, a t-butoxycarbonylamino group, a hydroxymethyl group, a 2- hydroxyethyl group, a 3-hydroxypropyl group, a 2-cyanoethoxy group, a (2-cyanoethoxy)methyl group, a 2-carbamoylethoxy group, an ethoxycarbonyl group, a t-butoxycarbonyl group, a benzoyloxy group, a phenylacetylamino group, a butanoylamino group, and a pentanoylamino group; among R⁵, R⁶, and R⁷, a group which is not involved in formation of the ring represents a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkenyl group having from 3 to 4 carbon atoms, or a straight chain alkynyl group having 3, 4, or 6 carbon atoms, and 1) the alkyl group, the alkenyl group, and the alkynyl group represented by R⁵, R⁶, or R⁷ are substituted with any one of a phenyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cyclopropyl group, a cyclopentyl group, a cyano group, a hydroxyl group, a carboxyl group, and an —SO₃H group, 2) the alkyl group, the alkenyl group, and the alkynyl group are substituted with two hydroxyl groups, 3) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group and one —SO₃H, 4) the alkyl group, the alkenyl group, and the alkynyl group are substituted with four hydroxyl groups and one oxo group, 5) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one nitro group and one morpholyl group, 6) one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by a —CO₂—, or 7) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one morpholyl group and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by an —O—, or the alkyl group, the alkenyl group, and the alkynyl group are neither substituted nor replaced, III) N⁺R⁵R⁶R⁷ represents any one of 1) a pyridinium ring substituted with any one of a cyano group, a phenyl group, a thienyl group, a pyridyl group, a methoxy group, an ethoxy group, a propoxy group, a carboxyl group, a —CONH₂ group, and a group, 2) a pyridinium ring substituted with two cyano groups, 3) a pyridinium ring substituted with two (—R¹²)s, 4) a pyridinium ring substituted with one cyano group and one —R¹², 5) a pyridinium ring substituted with one phenyl group and one R¹², 6) a quinolinium ring substituted with any one of a cyano group, a nitro group, a carboxyl group, a methoxy group, an ethoxy group, a propoxy group, and —R¹², 7) a quinolinium ring substituted with one methoxy group and one —R¹², 8) a quinolinium ring substituted with one nitro group and one —R¹², 9) an unsubstituted pyridinium ring, 10) an unsubstituted quinolinium ring, and 11) an unsubstituted isoquinolinium ring, where R¹² represents any one of a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a 3-pentyl group, a 5-nonyl group, a vinyl group, a benzyl group, a 3-phenylpropyl group, a 2-(1-naphthyl)vinyl group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3- hydroxypropyl group, a formyl group, an acetyl group, a propionyl group, a benzoyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, a hexoxycarbonyl group, a benzyloxycarbonyl group, a 2-propenyloxycarbonyl group, an ethoxycarbonylmethyl group, a 2-(methoxycarbonyl)ethyl group, an ethoxycarbonylmethylcarbonyl group, a 2- hydroxyethylaminocarbonyl group, a bis (2- hydroxyethyl)aminocarbonyl group, a 2-carboxyvinyl group, a carboxymethylthio group, a cyanomethyl group, a 2-nitrovinyl group, a 2-(4-pyridyl)ethyl group, a 2-(4-pyridyl)vinyl group, a 3-(4-pyridyl)propyl group, a 2-(4-pyridyl)-1,2-dihydroxyethyl group, and a 2-sulfoethyl group, provided that the position of its bonding with Z is an ammonium nitrogen atom.
 17. The compound according to claim 1, wherein N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent: I) R⁵, R⁶, and R⁷, which may be mutually different, each represents any one of a straight chain alkyl group having from 1 to 10 carbon atoms, a straight chain alkyl group having from 1 to 10 carbon atoms which is substituted with one phenyl group, a straight chain alkyl group having from 1 to 10 carbon atoms which is substituted with one hydroxyl group, a straight chain alkenyl group having from 3 to 6, or 8 carbon atoms, a branched alkenyl group having 4, 6, or 7 carbon atoms, a straight chain alkynyl group having 3, 5, 6, 7, or 9 carbon atoms, and a branched alkynyl group having 6 carbon atoms, II) N⁺R⁵R⁶R⁷ represents a pyrrolidinium ring, a piperidinium ring, an azepanium ring, a quinuclidinium ring, or a 1,4- diazabicyclo[2.2.2]-octanium ring, substituted with any one of a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-propenyl group, a phenyl group, a benzyl group, a hydroxyl group, a hydroxymethyl group, a 2- hydroxyethyl group, and a 3-hydroxypropyl group, or unsubstituted, provided that the position of its bonding with Z is an ammonium nitrogen atom; among R⁵, R⁶, and R⁷, a group which is not involved in formation of the ring represents any one of a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkyl group having from 1 to 6 carbon atoms which is substituted with one phenyl group, a straight chain alkyl group having from 1 to 6 carbon atoms which is substituted with one hydroxyl group, a straight chain alkenyl group having from 3 to 4 carbon atoms, and a straight chain alkynyl group having 3, 4, or 6 carbon atoms, III) N⁺R⁵R⁶R⁷ represents an unsubstituted pyridinium ring, an unsubstituted quinolinium ring, an unsubstituted isoquinolinium ring, a pyridinium ring substituted with any one of a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a vinyl group, a phenyl group, a benzyl group, a 3-phenylpropyl group, a hydroxymethyl group, a 2-hydroxyethyl group, and a 3- hydroxypropyl group, a pyridinium ring substituted with any one selected from two methyl groups or two ethyl groups, a pyridinium ring substituted with one phenyl group and one methyl group, or a quinolinium ring substituted with any one of a methyl group and an i-propyl group, provided that the position of its bonding with Z is ammonium nitrogen atom.
 18. The compound according to claim 15, wherein R¹ and R², which may be mutually different, each represents a straight chain alkyl group having 2 to 6 carbon atoms, and (NR³R⁴)_(m) represents any one of a dimethylamino group substituting at the 7-position, a diethylamino group substituting at the 7- position, an ethylmethylamino group substituting at the 7- position, a dimethylamino group substituting at the 9-position, and dimethylamino groups substituting at the 7- and 9-positions.
 19. The compound according to claim 16, wherein R¹ and R², which may be mutually different, each represents a straight chain alkyl group having 2 to 6 carbon atoms, and (NR³R⁴)_(m) represents any one of a dimethylamino group substituting at the 7-position, a diethylamino group substituting at the 7- position, an ethylmethylamino group substituting at the 7- position, a dimethylamino group substituting at the 9-position, and dimethylamino groups substituting at the 7- and 9-positions.
 20. The compound according to claim 17, wherein R¹ and R², which may be mutually different, each represents a straight chain alkyl group having 2 to 6 carbon atoms, and (NR³R⁴)_(m) represents any one of a dimethylamino group substituting at the 7-position, a diethylamino group substituting at the 7- position, an ethylmethylamino group substituting at the 7- position, a dimethylamino group substituting at the 9-position, and dimethylamino groups substituting at the 7- and 9-positions.
 21. The compound according to claim 18, wherein (NR³R⁴)_(m) represents any one of a dimethylamino group substituting at the 7-position, a diethylamino group substituting at the 7- position, and an ethylmethylamino group substituting at the 7- position, and N⁺R⁵R⁶R⁷ represents any one of a 4-t-butylpyridinium group, a 3-(3-hydroxypropyl)-pyridinium group, a 3-[2- (methoxycarbonyl)ethyl]-pyridinium group, a 2-(n-propyl)- pyridinium group, a 4-phenyiquinuclidinium group, and a 1,4- diazabicyclo[2.2.2]octanium group.
 22. A pharmaceutical composition containing the compound according to claim 1 as an active ingredient. 